The influence of chiral auxiliaries and catalysts on the selectivity of intramolecular conjugate additions of pyrrole to N-tethered Michael acceptors

被引：66

作者：

Banwell, MG ^{[1
]}

Beck, DAS ^{[1
]}

Smith, JA ^{[1
]}

机构：

[1] Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2004年 / 2卷 / 02期

关键词：

D O I：

10.1039/b312552a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of pyrroles incorporating N-tethered acrylates and related groups has been prepared and examined for their capacity to undergo intramolecular Michael addition reactions to form, in a diastereo- or enantio-selective fashion, the corresponding 8-substituted tetrahydroindolizidine or homologues thereof.

引用

页码：157 / 159

页数：3

共 26 条

[1]

[Anonymous], CATALYTIC ASYMMETRIC

[2]

Babu SA, 2002, SYNLETT, P531

[3] Total synthesis of (±)-rhazinal, an alkaloidal spindle toxin from Kopsia teoi [J].

Banwell, MG ;

Edwards, AJ ;

Jolliffe, KA ;

Smith, JA ;

Hamel, E ;

Verdier-Pinard, P .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (02) :296-305

[4] Exploiting multiple nucleophilic sites on pyrrole for the assembly of polyheterocyclic frameworks:: application to a formal total synthesis of (±)-aspidospermidine [J].

Banwell, MG ;

Smith, JA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (23) :2613-2618

[5] First syntheses of the pyrroloketopiperazine marine natural products (±)-longamide, (±)-longamide B, (±)-longamide B methyl ester and (±)-hanishin [J].

Banwell, MG ;

Bray, AM ;

Willis, AC ;

Wong, DJ .

NEW JOURNAL OF CHEMISTRY, 1999, 23 (07) :687-690

[6] New approaches to olefin cross-metathesis [J].

Blackwell, HE ;

O'Leary, DJ ;

Chatterjee, AK ;

Washenfelder, RA ;

Bussmann, DA ;

Grubbs, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (01) :58-71

[7] Synthesis of functionalized olefins by cross and ring-closing metatheses [J].

Chatterjee, AK ;

Morgan, JP ;

Scholl, M ;

Grubbs, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (15) :3783-3784

[8] Synthesis of trisubstituted alkenes via olefin cross-metathesis [J].

Chatterjee, AK ;

Grubbs, RH .

ORGANIC LETTERS, 1999, 1 (11) :1751-1753

[9] PREPARATION OF AN OPTICALLY-ACTIVE PROSTAGLANDIN INTERMEDIATE VIA ASYMMETRIC INDUCTION [J].

COREY, EJ ;

ENSLEY, HE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (23) :6908-6909

[10] Enamino ester reduction:: A short enantioselective route to pyrrolizidine and indolizidine alkaloids.: Synthesis of (+)-laburnine, (+)-tashiromine, and (-)-isoretronecanol [J].

David, O ;

Blot, J ;

Bellec, C ;

Fargeau-Bellassoued, MC ;

Haviari, G ;

Célérier, JP ;

Lhommet, G ;

Gramain, JC ;

Gardette, D .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) :3122-3131

← 1 2 3 →