char = R;code = 82 char = e;code = 101 char = g;code = 103 char = i;code = 105 char = o;code = 111 char = s;code = 115 char = e;code = 101 char = l;code = 108 char = e;code = 101 char = c;code = 99 char = t;code = 116 char = i;code = 105 char = v;code = 118 char = e;code = 101 char = ;code = 32 char = a;code = 97 char = l;code = 108 char = l;code = 108 char = e;code = 101 char = n;code = 110 char = e;code = 101 char = ;code = 32 char = s;code = 115 char = y;code = 121 char = n;code = 110 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = s;code = 115 char = i;code = 105 char = s;code = 115 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = p;code = 112 char = r;code = 114 char = o;code = 111 char = p;code = 112 char = a;code = 97 char = r;code = 114 char = g;code = 103 char = y;code = 121 char = l;code = 108 char = a;code = 97 char = t;code = 116 char = i;code = 105 char = o;code = 111 char = n;code = 110 char = s;code = 115 char = ;code = 32 char = w;code = 119 char = i;code = 105 char = t;code = 116 char = h;code = 104 char = ;code = 32 char = p;code = 112 char = r;code = 114 char = o;code = 111 char = p;code = 112 char = a;code = 97 char = r;code = 114 char = g;code = 103 char = y;code = 121 char = l;code = 108 char = ;code = 32 char = d;code = 100 char = i;code = 105 char = e;code = 101 char = t;code = 116 char = h;code = 104 char = a;code = 97 char = n;code = 110 char = o;code = 111 char = l;code = 108 char = a;code = 97 char = m;code = 109 char = i;code = 105 char = n;code = 110 char = e;code = 101 char = ;code = 32 char = b;code = 98 char = o;code = 111 char = r;code = 114 char = o;code = 111 char = n;code = 110 char = a;code = 97 char = t;code = 116 char = e;code = 101 char = s;code = 115 char = .;code = 46 result sql = Regioselective allene synthesis and propargylations with propargyl diethanolamine boronates.
Regioselective allene synthesis and propargylations with propargyl diethanolamine boronates.char = T;code = 84 char = h;code = 104 char = e;code = 101 char = ;code = 32 char = u;code = 117 char = t;code = 116 char = i;code = 105 char = l;code = 108 char = i;code = 105 char = t;code = 116 char = y;code = 121 char = ;code = 32 char = o;code = 111 char = f;code = 102 char = ;code = 32 char = p;code = 112 char = r;code = 114 char = o;code = 111 char = p;code = 112 char = a;code = 97 char = r;code = 114 char = g;code = 103 char = y;code = 121 char = l;code = 108 char = ;code = 32 char = d;code = 100 char = i;code = 105 char = e;code = 101 char = t;code = 116 char = h;code = 104 char = a;code = 97 char = n;code = 110 char = o;code = 111 char = l;code = 108 char = a;code = 97 char = m;code = 109 char = i;code = 105 char = n;code = 110 char = e;code = 101 char = ;code = 32 char = b;code = 98 char = o;code = 111 char = r;code = 114 char = o;code = 111 char = n;code = 110 char = a;code = 97 char = t;code = 116 char = e;code = 101 char = s;code = 115 char = ;code = 32 char = a;code = 97 char = s;code = 115 char = ;code = 32 char = r;code = 114 char = e;code = 101 char = a;code = 97 char = g;code = 103 char = e;code = 101 char = n;code = 110 char = t;code = 116 char = s;code = 115 char = ;code = 32 char = f;code = 102 char = o;code = 111 char = r;code = 114 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = ;code = 32 char = p;code = 112 char = r;code = 114 char = e;code = 101 char = p;code = 112 char = a;code = 97 char = r;code = 114 char = a;code = 97 char = t;code = 116 char = i;code = 105 char = o;code = 111 char = n;code = 110 char = ;code = 32 char = o;code = 111 char = f;code = 102 char = ;code = 32 char = a;code = 97 char = l;code = 108 char = l;code = 108 char = e;code = 101 char = n;code = 110 char = e;code = 101 char = s;code = 115 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = h;code = 104 char = o;code = 111 char = m;code = 109 char = o;code = 111 char = p;code = 112 char = r;code = 114 char = o;code = 111 char = p;code = 112 char = a;code = 97 char = r;code = 114 char = g;code = 103 char = y;code = 121 char = l;code = 108 char = i;code = 105 char = c;code = 99 char = ;code = 32 char = a;code = 97 char = l;code = 108 char = c;code = 99 char = o;code = 111 char = h;code = 104 char = o;code = 111 char = l;code = 108 char = s;code = 115 char = ;code = 32 char = i;code = 105 char = s;code = 115 char = ;code = 32 char = p;code = 112 char = r;code = 114 char = e;code = 101 char = s;code = 115 char = e;code = 101 char = n;code = 110 char = t;code = 116 char = e;code = 101 char = d;code = 100 char = .;code = 46 char = ;code = 32 char = P;code = 80 char = r;code = 114 char = o;code = 111 char = t;code = 116 char = o;code = 111 char = n;code = 110 char = o;code = 111 char = l;code = 108 char = y;code = 121 char = s;code = 115 char = i;code = 105 char = s;code = 115 char = ;code = 32 char = w;code = 119 char = i;code = 105 char = t;code = 116 char = h;code = 104 char = ;code = 32 char = T;code = 84 char = F;code = 70 char = A;code = 65 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = e;code = 101 char = l;code = 108 char = e;code = 101 char = c;code = 99 char = t;code = 116 char = r;code = 114 char = o;code = 111 char = p;code = 112 char = h;code = 104 char = i;code = 105 char = l;code = 108 char = i;code = 105 char = c;code = 99 char = ;code = 32 char = s;code = 115 char = u;code = 117 char = b;code = 98 char = s;code = 115 char = t;code = 116 char = i;code = 105 char = t;code = 116 char = u;code = 117 char = t;code = 116 char = i;code = 105 char = o;code = 111 char = n;code = 110 char = ;code = 32 char = w;code = 119 char = i;code = 105 char = t;code = 116 char = h;code = 104 char = ;code = 32 char = N;code = 78 char = -;code = 45 char = h;code = 104 char = a;code = 97 char = l;code = 108 char = o;code = 111 char = s;code = 115 char = u;code = 117 char = c;code = 99 char = c;code = 99 char = i;code = 105 char = n;code = 110 char = i;code = 105 char = m;code = 109 char = i;code = 105 char = d;code = 100 char = e;code = 101 char = s;code = 115 char = ;code = 32 char = p;code = 112 char = r;code = 114 char = o;code = 111 char = c;code = 99 char = e;code = 101 char = e;code = 101 char = d;code = 100 char = e;code = 101 char = d;code = 100 char = ;code = 32 char = w;code = 119 char = i;code = 105 char = t;code = 116 char = h;code = 104 char = ;code = 32 char = i;code = 105 char = n;code = 110 char = v;code = 118 char = e;code = 101 char = r;code = 114 char = s;code = 115 char = i;code = 105 char = o;code = 111 char = n;code = 110 char = ;code = 32 char = t;code = 116 char = o;code = 111 char = ;code = 32 char = p;code = 112 char = r;code = 114 char = o;code = 111 char = v;code = 118 char = i;code = 105 char = d;code = 100 char = e;code = 101 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = ;code = 32 char = c;code = 99 char = o;code = 111 char = r;code = 114 char = r;code = 114 char = e;code = 101 char = s;code = 115 char = p;code = 112 char = o;code = 111 char = n;code = 110 char = d;code = 100 char = i;code = 105 char = n;code = 110 char = g;code = 103 char = ;code = 32 char = a;code = 97 char = l;code = 108 char = l;code = 108 char = e;code = 101 char = n;code = 110 char = e;code = 101 char = ;code = 32 char = i;code = 105 char = n;code = 110 char = ;code = 32 char = h;code = 104 char = i;code = 105 char = g;code = 103 char = h;code = 104 char = ;code = 32 char = y;code = 121 char = i;code = 105 char = e;code = 101 char = l;code = 108 char = d;code = 100 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = r;code = 114 char = e;code = 101 char = g;code = 103 char = i;code = 105 char = o;code = 111 char = s;code = 115 char = e;code = 101 char = l;code = 108 char = e;code = 101 char = c;code = 99 char = t;code = 116 char = i;code = 105 char = v;code = 118 char = i;code = 105 char = t;code = 116 char = y;code = 121 char = .;code = 46 char = ;code = 32 char = A;code = 65 char = l;code = 108 char = t;code = 116 char = e;code = 101 char = r;code = 114 char = n;code = 110 char = a;code = 97 char = t;code = 116 char = i;code = 105 char = v;code = 118 char = e;code = 101 char = l;code = 108 char = y;code = 121 char = ,;code = 44 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = ;code = 32 char = p;code = 112 char = r;code = 114 char = o;code = 111 char = p;code = 112 char = a;code = 97 char = r;code = 114 char = g;code = 103 char = y;code = 121 char = l;code = 108 char = a;code = 97 char = t;code = 116 char = i;code = 105 char = o;code = 111 char = n;code = 110 char = ;code = 32 char = o;code = 111 char = f;code = 102 char = ;code = 32 char = a;code = 97 char = l;code = 108 char = d;code = 100 char = e;code = 101 char = h;code = 104 char = y;code = 121 char = d;code = 100 char = e;code = 101 char = s;code = 115 char = ;code = 32 char = w;code = 119 char = a;code = 97 char = s;code = 115 char = ;code = 32 char = a;code = 97 char = c;code = 99 char = h;code = 104 char = i;code = 105 char = e;code = 101 char = v;code = 118 char = e;code = 101 char = d;code = 100 char = ;code = 32 char = w;code = 119 char = i;code = 105 char = t;code = 116 char = h;code = 104 char = ;code = 32 char = u;code = 117 char = s;code = 115 char = e;code = 101 char = ;code = 32 char = o;code = 111 char = f;code = 102 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = ;code = 32 char = i;code = 105 char = n;code = 110 char = ;code = 32 char = s;code = 115 char = i;code = 105 char = t;code = 116 char = u;code = 117 char = ;code = 32 char = g;code = 103 char = e;code = 101 char = n;code = 110 char = e;code = 101 char = r;code = 114 char = a;code = 97 char = t;code = 116 char = e;code = 101 char = d;code = 100 char = ;code = 32 char = l;code = 108 char = i;code = 105 char = t;code = 116 char = h;code = 104 char = i;code = 105 char = a;code = 97 char = t;code = 116 char = e;code = 101 char = d;code = 100 char = ;code = 32 char = c;code = 99 char = o;code = 111 char = m;code = 109 char = p;code = 112 char = l;code = 108 char = e;code = 101 char = x;code = 120 char = .;code = 46 char = <;code = 60 char = b;code = 98 char = r;code = 114 char = /;code = 47 char = >;code = 62 result sql = The utility of propargyl diethanolamine boronates as reagents for the preparation of allenes and homopropargylic alcohols is presented. Protonolysis with TFA and electrophilic substitution with N-halosuccinimides proceeded with inversion to provide the corresponding allene in high yield and regioselectivity. Alternatively, the propargylation of aldehydes was achieved with use of the in situ generated lithiated complex.
Publication: Org. Lett. 2009 Dec 3 ;11(23)::5458-61. :doi: 10.1021/ol9022529.
Publication Date: 2009 Dec 3
Study Author(s): Fandrick, Daniel R;Reeves, Jonathan T;Tan, Zhulin;Lee, Heewon;Song, Jinhua J;Yee, Nathan K;Senanayake, Chris H;
Institution: Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., 900 Old Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, USA.
[email protected]
Shortcut link to this study:
The utility of propargyl diethanolamine boronates as reagents for the preparation of allenes and homopropargylic alcohols is presented. Protonolysis with TFA and electrophilic substitution with N-halosuccinimides proceeded with inversion to provide the corresponding allene in high yield and regioselectivity. Alternatively, the propargylation of aldehydes was achieved with use of the in situ generated lithiated complex.