Rearrangements and racemisation during the synthesis of L-serine derived oxazolidin-2-ones

被引：30
作者：
Bew, SP
Bull, SD
Davies, SG
Savory, ED
Watkin, DJ
机构：
[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England
[2] Univ Oxford, Dept Chem Crystallog, Oxford OX1 3PD, England
来源：
TETRAHEDRON | 2002年 / 58卷 / 46期
关键词：
racemisation; L-serine; oxazolidin-2-one;
D O I：
10.1016/S0040-4020(02)01223-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The propensity for N-Boc-4-hydroxymethyl-oxazolidin-2-ones to undergo rapid O-O and N-O carbonyl transfer makes these L-serine derived chiral auxiliaries unsuitable for attachment to polymers. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：9387 / 9401
页数：15
相关论文
共 37 条
[1]  
Ager DJ, 1996, SYNTHESIS-STUTTGART, P1283
[2]   The preparation and first application of a polymer-supported ''Evans'' oxazolidinone. [J].
Allin, SM ;
Shuttleworth, SJ .
TETRAHEDRON LETTERS, 1996, 37 (44) :8023-8026
[3]  
Avenoza A, 1997, SYNTHESIS-STUTTGART, P1146
[4]  
Bew SP, 2000, CHIRALITY, V12, P483, DOI 10.1002/(SICI)1520-636X(2000)12:5/6<483::AID-CHIR33>3.0.CO
[5]  
2-D
[6]   Polymer supported oxazolidin-2-ones derived from L-serine - a cautionary tale [J].
Bew, SP ;
Bull, SD ;
Davies, SG .
TETRAHEDRON LETTERS, 2000, 41 (39) :7577-7581
[7]   Total synthesis of luzopeptins A-C [J].
Boger, DL ;
Ledeboer, MW ;
Kume, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (05) :1098-1099
[8]   SuperQuat, (S)-4-benzyl-5,5-dimethyl-oxazolidin-2-one for the asymmetric synthesis of α-substituted aldehydes [J].
Bull, SD ;
Davies, SG ;
Nicholson, RL ;
Sanganee, HJ ;
Smith, AD .
TETRAHEDRON-ASYMMETRY, 2000, 11 (17) :3475-3479
[9]  
Bull SD, 1998, SYNLETT, P519
[10]   Asymmetric alkylations using SuperQuat auxiliaries - an investigation into the synthesis and stability of enolates derived from 5,5-disubstituted oxazolidin-2-ones [J].
Bull, SD ;
Davies, SG ;
Jones, S ;
Sanganee, HJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (04) :387-398
1234