Diastereoselection of the addition of silyloxyfurans to five-, six- and seven-membered N-acyliminium ions

被引：27

作者：

de Oliveira, MDF ^{[1
]}

Santos, LS ^{[1
]}

Pilli, RA ^{[1
]}

机构：

[1] Univ Estadual Campinas, Inst Quim, BR-13083970 Campinas, SP, Brazil

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 40期

基金：

巴西圣保罗研究基金会;

关键词：

D O I：

10.1016/S0040-4039(01)01388-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of silyloxyfuran 1a to five-, six- and seven-membered N-acyliminium ions 2 afforded threo-3 as the major isomers (the structures of 3a, 3g and 3m were determined by X-ray analysis). The diastereoisomeric ratio increased with bulkier carbamate groups (Boc>Cbz>CO2Me) with the five- and seven-membered N-acyliminium ions more selective than the six-membered ones. However. erythro-4 isomers predominated when 5-methylsilyloxyfuran 1b was employed (the structures were determined by NOE studies on the corresponding bicyclic lactams 6a.b and 7a,b) and the formation or regioisomer 5 was observed for N-acyliminium ions with Boc (seven-membered series) and Cbz (six- and seven-membered series) groups. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：6995 / 6997

页数：3

共 14 条

[1] 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

[2] The addition of 2-tert-butyldimethylsilyloxyfuran to cyclic N-acyliminium ions containing cyclohexyl-based chiral auxiliaries [J].

D'Oca, MGM ;

Pilli, RA ;

Vencato, I .

TETRAHEDRON LETTERS, 2000, 41 (50) :9709-9712

[3]

MARTIN SF, 1992, SYNTHESIS-STUTTGART, P55

[4] Applications of vinylogous Mannich reactions. Concise enantiospecific total syntheses of (+)-croomine [J].

Martin, SF ;

Barr, KJ ;

Smith, DW ;

Bur, SK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (30) :6990-6997

[5] AN EFFICIENT APPROACH TOWARD PYRROLIDINYLLACTONE SYSTEM CHARACTERISTIC OF THE STEMONA ALKALOIDS - LEWIS-ACID CATALYZED STEREOSELECTIVE REACTION OF N-BENZYLOXYCARBONYL-2-METHOXYPYRROLIDINE WITH 3-METHYL-2-TRIMETHYLSILYLOXYFURAN [J].

MORIMOTO, Y ;

NISHIDA, K ;

HAYASHI, Y ;

SHIRAHAMA, H .

TETRAHEDRON LETTERS, 1993, 34 (36) :5773-5776

[6]

MORIMOTO Y, 1995, SYNLETT, P1221

[7] C-glycosylation of cyclic N-acyliminium ions with trimethylsilyloxyfuran [J].

Pichon, M ;

Figadere, B ;

Cave, A .

TETRAHEDRON LETTERS, 1996, 37 (44) :7963-7966

[8] Addition of a chiral boron enolate to cyclic N-acyliminium ions. Stereocontrolled synthesis of the pyrrolizidine ring system [J].

Pilli, RA ;

Russowsky, D .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09) :3187-3190

[9] Recent progress in the chemistry of the Stemona alkaloids [J].

Pilli, RA ;

de Oliveira, MDCF .

NATURAL PRODUCT REPORTS, 2000, 17 (01) :117-127

[10] The stereochemistry of the addition of titanium enolates of N-propionyl-oxazolidin-2-ones to 5- and 6-membered N-acyliminium ions [J].

Pilli, RA ;

Alves, CD ;

Böckelmann, MA ;

Mascarenhas, YP ;

Nery, JG ;

Vencato, I .

TETRAHEDRON LETTERS, 1999, 40 (15) :2891-2894

← 1 2 →