Addition of carbon nucleophiles to substituted N-acyliminium ions.: A stereoselective route to trans-fused decahydroquinoline systems

被引：14

作者：

Maldaner, AO ^{[1
]}

Pilli, RA ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 41期

基金：

巴西圣保罗研究基金会;

关键词：

N-acyliminium ions; metathesis; piperidinones; decahydroquinolines;

D O I：

10.1016/S0040-4039(00)01362-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective route to trans-fused 2-substituted decahydroquinoline hydrochloride 11 featuring the addition of allyl tri-n-butyltin to a disubstituted N-acyliminium ion derived from glutarimide, followed by ring-closing metathesis is described (seven steps, 13% overall yield from lactam 4). (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：7843 / 7846

页数：4

共 28 条

[1] Addition of carbon nucleophiles to cyclic N-acyliminium ions in SDS/water
Camilo, NS
Pilli, RA
TETRAHEDRON LETTERS, 2004, 45 (13) : 2821 - 2823
[2] STEREOSELECTIVE ADDITION OF ORGANOCOPPER REAGENTS TO CYCLIC N-ACYLIMINIUM IONS
LUDWIG, C
WISTRAND, LG
ACTA CHEMICA SCANDINAVICA, 1994, 48 (04): : 367 - 371
[3] Stereoselective synthesis of trans-2,3-disubstituted pyrrolidines via addition to N-acyliminium ions
Buezo, ND
Jiménez, A
Pedregal, C
Vidal, P
TETRAHEDRON LETTERS, 2006, 47 (15) : 2489 - 2492
[4] INTRAMOLECULAR REACTIONS OF 2-PROPYNYLSILANES WITH N-ACYLIMINIUM IONS - CUPRATE SN2' REACTIONS OF THE ALLENIC PRODUCTS AS A ROUTE TO TRANS-FUSED CARBOBICYCLES
KLAVER, WJ
MOOLENAAR, MJ
HIEMSTRA, H
SPECKAMP, WN
TETRAHEDRON, 1988, 44 (13) : 3805 - 3818
[5] Highly stereoselective trans addition of π-type nucleophiles to a bicyclic N-acyliminium ion -: Application to the synthesis of indolizidine and pyrrolizidine alkaloids
Dhimane, H
Vanucci-Bacque, C
Hamon, L
Lhommet, G
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1998, 1998 (09) : 1955 - 1963
[6] Addition of carbon nucleophiles to cyclic N-acyliminium and oxocarbenium ions under solvent-free conditions
de Godoy, Luiz Antonio F.
Camilo, Nilton Soares
Pilli, Ronaldo Aloise
TETRAHEDRON LETTERS, 2006, 47 (45) : 7853 - 7856
[7] Addition of silylated carbon nucleophiles to iminium and cyclic N-acyliminium ions promoted by InCl3
Russowsky, D
Petersen, RZ
Godoi, MN
Pilli, RA
TETRAHEDRON LETTERS, 2000, 41 (51) : 9939 - 9942
[8] Enhanced trans diastereoselection in the allylation of cyclic chiral N-acyliminium ions.: Synthesis of hydroxylated indolizidines
Klitzke, CF
Pilli, RA
TETRAHEDRON LETTERS, 2001, 42 (33) : 5605 - 5608
[9] HIGHLY STEREOSELECTIVE ADDITION OF ALKYLCOPPER REAGENTS TO N-ACYLIMINIUM IONS - ENANTIOSELECTIVE SYNTHESIS OF TRANS-2-BUTYL-5-HEPTYLPYRROLIDINE
SKRINJAR, M
WISTRAND, LG
TETRAHEDRON LETTERS, 1990, 31 (12) : 1775 - 1778
[10] CHIROSPECIFIC SYNTHESIS OF TRANS-2,5-DISUBSTITUTED PYRROLIDINES VIA STEREOSELECTIVE ADDITION OF ORGANOCOPPER REAGENTS TO N-ACYLIMINIUM IONS
WISTRAND, LG
SKRINJAR, M
TETRAHEDRON, 1991, 47 (4-5) : 573 - 582

← 1 2 3 →