Stereoselective synthesis of 2-aryloxy acids from lactamide derived esters of racemic alpha-halo carboxylic acids.

被引：34

作者：

Devine, PN

Dolling, UH

Heid, RM

Tschaen, DM

机构：

[1] Department of Process Research, Merck Research Laboratories, Division of Merck and Co., Inc., Rahway, NJ 07065

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 16期

关键词：

D O I：

10.1016/0040-4039(96)00391-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pyrolidine derived (S)-lactamide auxiliaries mediate a highly stereoselective coupling reaction between racemic alpha-haloacids and aryloxides. These amide auxiliaries exhibit enhanced rates of reaction as well as increased degrees of diasteroselection over conventional ester auxiliaries. Copyright (C) Elsevier Science Ltd.

引用

页码：2683 / 2686

页数：4

共 11 条

[1] [Anonymous], TOTAL SYNTHESIS NATU
[2] BASHA A, 1977, TETRAHEDRON LETT, V28, P4171
[3] A NEW PROCESS FOR THE ENANTIOSELECTIVE SYNTHESIS OF CHIRAL ALPHA-ARYLOXY AND ALPHA-HYDROXY ACIDS
COREY, EJ
LINK, JO
[J]. TETRAHEDRON LETTERS, 1992, 33 (24) : 3431 - 3434
[4] ASYMMETRIC-SYNTHESIS OF ALPHA-HALO ESTERS
DURST, T
KOH, K
[J]. TETRAHEDRON LETTERS, 1992, 33 (45) : 6799 - 6802
[5] EFFICIENT ALPHA-HALOGENATION OF ACYL CHLORIDES BY N-BROMOSUCCINIMIDE, N-CHLOROSUCCINIMIDE, AND MOLECULAR IODINE
HARPP, DN
BAO, LQ
BLACK, CJ
GLEASON, JG
SMITH, RA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (23) : 3420 - 3427
[6] NOVEL SYNTHESES OF THE CARBAPENEM KEY INTERMEDIATES, (3R,4R)-4-ACETOXY-3-[(R)-1-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]-2-AZETIDINONE AND (3S,4R)-3-[(R)-1-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]-4-CARBOXYMETHYL-2-AZETIDINONE, FROM (S)-ETHYL LACTATE
ITO, Y
KOBAYASHI, Y
KAWABATA, T
TAKASE, M
TERASHIMA, S
[J]. TETRAHEDRON, 1989, 45 (18) : 5767 - 5790
[7] REACTION OF (R)-PANTOLACTONE ESTERS OF ALPHA-BROMOACIDS WITH AMINES - A REMARKABLE SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-AMINO ESTERS
KOH, K
BEN, RN
DURST, T
[J]. TETRAHEDRON LETTERS, 1993, 34 (28) : 4473 - 4476
[8] STEREOSELECTIVE S(N)2 REACTIONS OF THE (R)-PANTOLACTONE ESTER OF RACEMIC ALPHA-HALO CARBOXYLIC-ACIDS WITH ARYLOXIDES - A SYNTHESIS OF (S)-2-ARYLOXY AND (S)-2-HYDROXY ACIDS
KOH, K
DURST, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (16) : 4683 - 4686
[9] KOK K, 1994, TETRAHEDRON LETT, V35, P375
[10] ALPHA-HYDROXY ESTERS AS CHIRAL REAGENTS - ASYMMETRIC-SYNTHESIS OF 2-ARYLPROPIONIC ACIDS
LARSEN, RD
CORLEY, EG
DAVIS, P
REIDER, PJ
GRABOWSKI, EJJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (19) : 7650 - 7651

← 1 2 →