Allenylmethylsilanes as nucleophiles in N-acyliminium ion chemistry

被引：40

作者：

Mentink, G ^{[1
]}

van Maarseveen, JH ^{[1
]}

Hiemstra, H ^{[1
]}

机构：

[1] Univ Amsterdam, Inst Mol Chem, NL-1018 WS Amsterdam, Netherlands

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 20期

关键词：

D O I：

10.1021/ol026615d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Treatment of a variety of N-acyliminium ion precursors with 2,3-butadienyl(trimethyl)si lane and related allenes in the presence of SF3-OEt2 provides good yields of N-protected 2-(aminomethyl)-substituted 1,3-dienes, which prove to be useful substrates for subsequent Diels-Alder and alkene metathesis reactions.

引用

页码：3497 / 3500

页数：4

共 35 条

[1] CARBON-CARBON BOND FORMATION VIA N-TOSYLIMINIUM IONS
AHMAN, J
SOMFAI, P
[J]. TETRAHEDRON, 1992, 48 (43) : 9537 - 9544
[2] Bear BR, 2001, ANGEW CHEM INT EDIT, V40, P821
[3] GAMMA-GLUTAMYLPEPTIDES FROM PHILADELPHUS-CORONARIUS
CAMPOS, L
MARLIER, M
DARDENNE, G
CASIMIR, J
[J]. PHYTOCHEMISTRY, 1983, 22 (11) : 2507 - 2508
[4] BETA-LACTAMS FROM CHIRALLY-ENRICHED (ALLENYLMETHYL)SILANES
COLVIN, EW
KONIG, WA
LORETO, MA
ROWDEN, JY
TOMMASINI, I
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (11) : 2405 - 2408
[5] BETA-LACTAMS FROM ALLYL-SILANES AND (ALLENYLMETHYL)-SILANES
COLVIN, EW
MONTEITH, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (18) : 1230 - 1232
[6] Silyl-substituted cyclopropyl carbenoids
Creary, X
Jiang, ZQ
Butchko, M
McLean, K
[J]. TETRAHEDRON LETTERS, 1996, 37 (05) : 579 - 582
[7] SYNTHESIS AND STEREOCHEMISTRY OF ALLENES .3. HIGHLY STEREOSELECTIVE SYNTHESIS OF CHIRAL ALKYLALLENES BY ORGANOCOPPER(I)-INDUCED ANTI 1,3-SUBSTITUTION OF CHIRAL PROPYNYL ESTERS
ELSEVIER, CJ
VERMEER, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (15) : 3726 - 3730
[8] Fleming I., 1989, ORG REACTIONS, V37, P57
[9] Fürstner A, 2000, ANGEW CHEM INT EDIT, V39, P3012
[10] Fürstner A, 2001, CHEM-EUR J, V7, P3236, DOI 10.1002/1521-3765(20010803)7:15<3236::AID-CHEM3236>3.0.CO

← 1 2 3 4 →