Exceptionally high Felkin-Anh control for the addition of nucleophiles to a beta-aminocyclopropylcarbaldehyde

被引：14

作者：

Bubert, C

Reiser, O

机构：

[1] UNIV STUTTGART,INST ORGAN CHEM,D-70569 STUTTGART,GERMANY

[2] UNIV GOTTINGEN,INST ORGAN CHEM,D-37077 GOTTINGEN,GERMANY

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 28期

关键词：

D O I：

10.1016/S0040-4039(97)01065-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Exceptionally high diastereocontrol in agreement with the Felkin-Anh model was observed for the addition of nucleophiles to the beta-aminocyclopropylcarbaldehyde 5 in nitroaldol, cyanohydrin, Mukaiyama aldol, and Sakurai reactions, contrasting the low diastereoselectivities generally observed in additions to cyclopropylcarbaldehydes. (C) 1997 Elsevier Science Ltd.

引用

页码：4985 / 4988

页数：4

共 25 条

[1] POTENTIAL GABA-B RECEPTOR ANTAGONISTS .7. THE SYNTHESIS OF 2-(4-CHLOROPHENYL)-3-NITROPROPAN-1-AMINE AND RELATED ANALOGS OF BACLOFEN
ABBENANTE, G
HUGHES, R
PRAGER, RH
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (08) : 1441 - 1452
[2] ANTCZAK K, 1984, CAN J CHEM, V63, P993
[3] HIGH-AFFINITY ANALOGS OF NEUROPEPTIDE-Y CONTAINING CONFORMATIONALLY RESTRICTED NON-PROTEINOGENIC AMINO-ACIDS
BECKSICKINGER, AG
HOFFMAN, E
PAULINI, K
REISSIG, HU
WILLIM, KD
WIELAND, HA
JUNG, G
[J]. BIOCHEMICAL SOCIETY TRANSACTIONS, 1994, 22 (01) : 145 - 149
[4] BUBERT C, 1994, SYNLETT, P675
[5] A GAMMA-TURN STRUCTURE INDUCED BY 2S,3S-2,3-METHANOMETHIONINE
BURGESS, K
HO, KK
PETTITT, BM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (02) : 799 - 800
[6] CONFORMATIONAL EFFECTS OF SUBSTITUTING METHIONINE WITH (2S,3S)-2,3-METHANOMETHIONINE IN PHE-MET-ARG-PHE-NH2
BURGESS, K
HO, KK
PETTITT, BM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (01) : 54 - 65
[7] BUSCH K, 1992, TETRAHEDRON, V48, P5607
[8] CABRELE C, UNPUB
[9] DEMEIJERE A, 1997, HOUBEN WEYL METH E A, V17
[10] SYNTHESIS AND THERMAL OR IONIC ISOMERIZATION OF VINYLCYCLOPROPYLCARBINOLS
DESCOTES, G
MENET, A
COLLONGE.F
[J]. TETRAHEDRON, 1973, 29 (18) : 2931 - 2935

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