Tandem electrophilic and nucleophilic additions to bicyclic tert-butyldimethylsilyloxypyrrole derived from (S)-pyroglutaminol

被引：17

作者：

Langlois, N ^{[1
]}

Choudhury, PK ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 13期

关键词：

D O I：

10.1016/S0040-4039(99)00284-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The silyloxypyrrole derivative 3, treated with SnCl4 and aqueous NaHCO3, afforded the 5-hydroxylated pyrrolidinone 7. This compound was shown to be a key intermediate for the diastereoselective introduction of other hetero- and C-nucleophiles at the same position. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2525 / 2528

页数：4

共 18 条

[1] Asymmetric routes towards polyfunctionalized pyrrolidines: Synthesis and reactivity of a chiral silyloxypyrrole. [J].

Baussanne, I ;

Royer, J .

TETRAHEDRON LETTERS, 1996, 37 (08) :1213-1216

[2]

CASIRAGH G, 1998, 18 EUR C HET CHEM 4

[3] FURAN-BASED, PYRROLE-BASED, AND THIOPHENE-BASED SILOXYDIENES FOR SYNTHESES OF DENSELY FUNCTIONALIZED HOMOCHIRAL COMPOUNDS [J].

CASIRAGHI, G ;

RASSU, G .

SYNTHESIS-STUTTGART, 1995, (06) :607-626

[4] N-(TERT-BUTOXYCARBONYL)-2-(TERT-BUTYLDIMETHYLSILOXY)PYRROLE - A PROMISING COMPOUND FOR SYNTHESIS OF CHIRAL NONRACEMIC HYDROXYLATED PYRROLIDINE DERIVATIVES [J].

CASIRAGHI, G ;

RASSU, G ;

SPANU, P ;

PINNA, L .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) :3760-3763

[5]

CHIARONI A, IN PRESS

[6] REGIOSELECTIVE FUNCTIONALIZATION OF HETEROCYCLIC RINGS - SYNTHESIS AND REACTIONS OF 1-METHYL-2-(TRIMETHYLSILOXY) PYRROLE AND 2-(TRIMETHYLSILOXY)THIOPHENE [J].

FIORENZA, M ;

REGINATO, G ;

RICCI, A ;

TADDEI, M ;

DEMBECH, P .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (03) :551-553

[7] EPOLACTAENE, A NOVEL NEURITOGENIC COMPOUND HUMAN NEUROBLASTOMA-CELLS, PRODUCED BY A MARINE FUNGUS [J].

KAKEYA, H ;

TAKAHASHI, I ;

OKADA, G ;

ISONO, K ;

OSADA, H .

JOURNAL OF ANTIBIOTICS, 1995, 48 (07) :733-735

[8] NEW SYNTHESES OF BETA-ALKOXY KETONES AND BETA-KETO ACETALS [J].

MUKAIYAMA, T ;

HAYASHI, M .

CHEMISTRY LETTERS, 1974, (01) :15-16

[9]

MUKAIYAMA T, 1982, ORG REACTIONS, V28, P203

[10]

Nagasaka T, 1997, CHEM PHARM BULL, V45, P36

← 1 2 →