Synthesis and enantioselective rearrangement of 4-amino-substituted cyclopentene oxides

被引：18

作者：

O'Brien, P ^{[1
]}

Towers, TD ^{[1
]}

Voith, M ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 44期

关键词：

epoxidation; diastereoselection; rearrangements; enantioselection;

D O I：

10.1016/S0040-4039(98)01821-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several N-mono- and diprotected alkenes have been prepared and the, stereoselectivity of their epoxidation has been investigated: N-monoprotected alkenes give cis epoxides preferentially (due to hydrogen bonding directed epoxidations) whereas N-diprotected alkenes produce trans epoxides exclusively (due to steric effects). Chiral lithium amide base-mediated rearrangement of a cis-monoprotected epoxide generated the corresponding amino-cyclopentenol in good yield and with an enantiomeric excess of 60%. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：8175 / 8178

页数：4

共 50 条

[31] Enantioselective synthesis of anti-β-substituted γ,δ-unsaturated amino acids:: A highly selective asymmetric thio-claisen rearrangement
Liu, Zhihua
Qu, Hongchang
Gu, Xuyuan
Min, Byoung J.
Nyberg, Joel
Hruby, Victor J.
ORGANIC LETTERS, 2008, 10 (18) : 4105 - 4108
[32] ENANTIOSELECTIVE SYNTHESIS OF 4'-SUBSTITUTED 2'-DEOXYRIBONUCLEOSIDE
KRISHNAMURTHY, N
JOHNSON, CR
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 206 : 306 - ORGN
[33] ENANTIOSELECTIVE SYNTHESIS OF (1R,4S)-1-AMINO-4-(HYDROXYMETHYL)-2-CYCLOPENTENE A PRECURSOR FOR CARBOCYCLIC NUCLEOSIDE SYNTHESIS
PARK, KH
RAPOPORT, H
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (02): : 394 - 399
[34] REGIOSELECTIVE ADDITION OF NITRILE-STABILIZED CARBANIONS TO 4-AMINO-SUBSTITUTED INDOLE CHROMIUM COMPLEXES AND THE TOTAL SYNTHESIS OF (-)-INDOLACTAM-V
SEMMELHACK, MF
RHEE, H
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 202 : 10 - ORGN
[35] SYNTHESIS OF VERSATILE INTERMEDIATES FOR CYCLOPENTANOID NATURAL-PRODUCTS VIA ENANTIOSELECTIVE DEPROTONATION OF SUBSTITUTED CYCLOPENTENE OXIDE
BHUNIYA, D
GUPTA, AD
SINGH, VK
TETRAHEDRON LETTERS, 1995, 36 (16) : 2847 - 2850
[36] Modifications of 4-Amino-substituted 5-Phenyl-3-(trifluoromethyl)pyrazoles for the Development of New Analgesics
Shchegolkov, Evgeny V.
Perminova, Anastasia N.
Malkova, Natalia A.
Kushch, Svetlana O.
Burgart, Yanina V.
Triandafilova, Galina A.
Solodnikov, Sergey Yu.
Krasnykh, Olga P.
Saloutin, Victor I.
CHEMISTRYSELECT, 2023, 8 (47):
[37] On the mechanism of lithium amide-induced rearrangements of 4-substituted cyclopentene oxides to cyclopentenols
Hodgson, DM
Gibbs, AR
TETRAHEDRON LETTERS, 1997, 38 (51) : 8907 - 8910
[38] 4-Amino-substituted 5-resorcinol-isoxazole derivatives, a novel class of Hsp90 inhibitor: Synthesis and evaluation of in vitro activity
Giannini, Giuseppe
Cabri, Walter
Brunetti, Tiziana
Ciacci, Andrea
Simoni, Daniele
Baruchello, Riccardo
Grisolia, Giuseppina
Rullo, Cinzia
Vesci, Loredana
Castorina, Massimo
Milazzo, Ferdinando Maria
Carminati, Paolo
Pisano, Claudio
CANCER RESEARCH, 2010, 70
[39] Enantioselective α-silyl amino acid synthesis by reverse-aza-brook rearrangement
Liu, GD
Sieburth, SM
ORGANIC LETTERS, 2003, 5 (24) : 4677 - 4679
[40] Synthetic applications of the amino-Cope rearrangement: enantioselective synthesis of some tetrahydropyrans
Allin, SM
Baird, RD
Lins, RJ
TETRAHEDRON LETTERS, 2002, 43 (23) : 4195 - 4197

← 1 2 3 4 5 →