Double asymmetric induction as a mechanistic probe: conjugate addition for the asymmetric synthesis of a pseudotripeptide

被引：31

作者：

Davies, SG ^{[1
]}

Hermann, GJ ^{[1
]}

Sweet, MJ ^{[1
]}

Smith, AD ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

来源：

CHEMICAL COMMUNICATIONS | 2004年 / 09期

关键词：

D O I：

10.1039/b401293c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Double asymmetric induction as a mechanistic probe indicates that, for the conjugate addition of (R)- and (S)-lithium N-benzyl-N-alpha-methylbenzylamide to (S)-3'-phenylprop-2'-enoyl-4-benzyloxazolidinone, the reactive conformation of the N-acyl oxazolidinone is the anti-s-cis form, facilitating the asymmetric synthesis of a pseudotripeptide.

引用

页码：1128 / 1129

页数：2

共 31 条

[1] LEWIS ACID-PROMOTED 1,4-ADDITION TO CHIRAL IMIDE DERIVATIVES IN THE SYNTHESIS OF BETA-AMINO ACIDS [J].

AMOROSO, R ;

CARDILLO, G ;

SABATINO, P ;

TOMASINI, C ;

TRERE, A .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (21) :5615-5619

[2] METAL-AMIDES IN ORGANIC-SYNTHESIS .7. STEREODIVERGENT SYNTHESIS OF THE ENOLATES OF A BETA-AMINO ESTER BY USING LITHIUM N-BENZYLTRIMETHYLSILYLAMIDE [J].

ASAO, N ;

UYEHARA, T ;

YAMAMOTO, Y .

TETRAHEDRON, 1990, 46 (13-14) :4563-4572

[3] STEREOSELECTIVE CONJUGATE ADDITION OF TMSI-ACTIVATED BUTYLCOPPER TO 1-(R)-ENDO-(1-NAPHTHYL)BORNYL CROTONATE [J].

BERGDAHL, M ;

NILSSON, M ;

OLSSON, T .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 391 (02) :C19-C22

[4] DIASTEREOSELECTIVITY IN IODOTRIMETHYLSILANE-PROMOTED CONJUGATE ADDITIONS OF ORGANOCOPPER REAGENTS TO CHIRAL ALPHA,BETA-UNSATURATED IMIDES AND AMIDES [J].

BERGDAHL, M ;

ILIEFSKI, T ;

NILSSON, M ;

OLSSON, T .

TETRAHEDRON LETTERS, 1995, 36 (18) :3227-3230

[5] Enone structure as a probe to Lewis acid carbonyl binding in copper-catalysed asymmetric conjugate addition [J].

Börner, C ;

König, WA ;

Woodward, S .

TETRAHEDRON LETTERS, 2001, 42 (02) :327-329

[6] Synthesis of N-acyl-β-aminoalcohols from N-acyloxazolidinones mediated by sodium azide [J].

Bouzide, A ;

Sauvé, G .

TETRAHEDRON LETTERS, 2002, 43 (11) :1961-1964

[7] NMR investigations on boron complexes in the conjugate addition on α,β-unsaturated imides [J].

Cardillo, G ;

Gentilucci, L ;

Gianotti, M ;

Tolomelli, A .

ORGANIC LETTERS, 2001, 3 (08) :1165-1167

[8] ET2ALCL COMPLEXES OF AN N-ACYLOXAZOLIDINONE - NMR INVESTIGATION [J].

CASTELLINO, S ;

DWIGHT, WJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (07) :2986-2987

[9] ASYMMETRIC-SYNTHESIS OF ANTI-ALPHA-ALKYL-BETA-AMINO ACIDS [J].

DAVIES, SG ;

WALTERS, IAS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (09) :1129-1139

[10]

DAVIES SG, 1995, RECL TRAV CHIM PAY B, V114, P175

← 1 2 3 4 →