STEREOSELECTIVITY IN THE CONDENSATION-REACTIONS BETWEEN MALATE ENOLATE AND IMINES TO 2-PYRROLIDINONE DERIVATIVES

被引：7

作者：

HA, DC

YUN, KS

PARK, HS

CHOUNG, WK

KWON, YE

机构：

[1] Department of Chemistry, Korea University, Seoul, 136-701

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 46期

关键词：

D O I：

10.1016/0040-4039(95)01818-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enolate dianion of diethyl (S)-malate was stereoselectively condensed with nonenolizable N-arylimines to give 2-pyrrolidinone derivatives. The presence of HMPA changes the diastereoselectivity of this cyclization reaction.

引用

页码：8445 / 8448

页数：4

共 21 条

[1] ORIGIN OF PI-FACIAL STEREOSELECTIVITY IN ADDITIONS TO PI-BONDS - GENERALITY OF THE ANTI-PERIPLANAR EFFECT
CARAMELLA, P
RONDAN, NG
PADDONROW, MN
HOUK, KN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (09) : 2438 - 2440
[2] DAI WM, 1990, HETEROCYCLES, V30, P1231
[3] STEREOSPECIFIC SYNTHESIS OF RACEMIC DAUNOSAMINE - DIASTEREOFACIAL SELECTIVITY IN A NITRONE CYCLOADDITION
DESHONG, P
LEGINUS, JM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (06) : 1686 - 1688
[4] ELIEL EL, 1994, STEREOCHEMISTRY ORGA, P835
[5] THE ESTER ENOLATE IMINE CONDENSATION ROUTE TO BETA-LACTAMS
HART, DJ
HA, DC
[J]. CHEMICAL REVIEWS, 1989, 89 (07) : 1447 - 1465
[6] THEORETICAL-STUDIES OF STEREOSELECTIVE HYDROBORATIONS
HOUK, KN
RONDAN, NG
WU, YD
METZ, JT
PADDONROW, MN
[J]. TETRAHEDRON, 1984, 40 (12) : 2257 - 2274
[7] STEREOSELECTIVE NITRILE OXIDE CYCLO-ADDITIONS TO CHIRAL ALLYL ETHERS AND ALCOHOLS - THE INSIDE ALKOXY EFFECT
HOUK, KN
MOSES, SR
WU, YD
RONDAN, NG
JAGER, V
SCHOHE, R
FRONCZEK, FR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (13) : 3880 - 3882
[8] RECENT ADVANCES IN THE SYNTHESIS OF PYRROLIZIDINES
IKEDA, M
SATO, T
ISHIBASHI, H
[J]. HETEROCYCLES, 1988, 27 (06) : 1465 - 1487
[9] THE DIANION CLAISEN REARRANGEMENT OF BETA-HYDROXY ESTERS
KURTH, MJ
YU, CM
[J]. TETRAHEDRON LETTERS, 1984, 25 (44) : 5003 - 5006
[10] ACYCLIC STEREOCONTROL THROUGH THE DIANIONIC CLAISEN REARRANGEMENT OF BETA-HYDROXY ESTERS - SYNTHESIS OF (+/-)-BOTRYODIPLODIN
KURTH, MJ
YU, CM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (11) : 1840 - 1845

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