Enantioselective cyclization/hydrosilylation of 1,6-enynes catalyzed by a cationic rhodium bis(phosphine) complex

被引：68

作者：

Chakrapani, H ^{[1
]}

Liu, C ^{[1
]}

Widenhoefer, RA ^{[1
]}

机构：

[1] Duke Univ, PM Gross Chem Lab, Durham, NC 27708 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 02期

关键词：

D O I：

10.1021/ol027196n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Reaction of 4,4-dicarbomethoxy-1-octene-6-yne (1) with triethylsilane and a catalytic 1:1 mixture of [Rh(COD)(2)](+) SbF6- and (R)-BIPHEMP (5 mol %) at 70 degreesC for 90 min gave (2)-1,1-dicarbomethoxy-3-(l-triethylsilyl)ethylidene-4-methylcyclopentane (2) in 81% isolated yield with 98% de and 92% ee.

引用

页码：157 / 159

页数：3

共 29 条

[1] ASYMMETRIC CATALYSIS - ASYMMETRIC CATALYTIC INTRAMOLECULAR HYDROACYLATION OF 4-PENTENALS USING CHIRAL RHODIUM DIPHOSPHINE CATALYSTS
BARNHART, RW
WANG, XQ
NOHEDA, P
BERGENS, SH
WHELAN, J
BOSNICH, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) : 1821 - 1830
[2] ASYMMETRIC CATALYSIS - PRODUCTION OF CHIRAL DIOLS BY ENANTIOSELECTIVE CATALYTIC INTRAMOLECULAR HYDROSILATION OF OLEFINS
BERGENS, SH
NOHEDA, P
WHELAN, J
BOSNICH, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (06) : 2121 - 2128
[3] Cao P, 2000, ANGEW CHEM INT EDIT, V39, P4104, DOI 10.1002/1521-3773(20001117)39:22<4104::AID-ANIE4104>3.0.CO
[4] 2-X
[5] ANIONIC APPROACHES TO THE CONSTRUCTION OF CYCLOPENTANOIDS
HUDLICKY, T
PRICE, JD
[J]. CHEMICAL REVIEWS, 1989, 89 (07) : 1467 - 1486
[6] Transition metal-mediated cycloaddition reactions
Lautens, M
Klute, W
Tam, W
[J]. CHEMICAL REVIEWS, 1996, 96 (01) : 49 - 92
[7] Cyclization/hydrosilylation of functionalized diynes catalyzed by a cationic rhodium bis(phosphine) complex
Liu, C
Widenhoefer, RA
[J]. ORGANOMETALLICS, 2002, 21 (25) : 5666 - 5673
[8] Cyclization/hydrosilylation of functionalized diynes catalyzed by a cationic platinum phenanthroline complex
Madine, JW
Wang, X
Widenhoefer, RA
[J]. ORGANIC LETTERS, 2001, 3 (03) : 385 - 388
[9] Sequential cyclization/silylation of enynes catalyzed by an organoyttrium complex
Molander, GA
Retsch, WH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (38) : 8817 - 8825
[10] Stereoselective synthesis of carbobicyclics via organoyttrium-catalyzed sequential cyclization/silylation reactions
Molander, GA
Nichols, PJ
Noll, BC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07) : 2292 - 2306

← 1 2 3 →