Desymmetrization by direct cross-metathesis producing hitherto unreachable P-stereogenic phosphine oxides

被引:21
作者
Bisaro, F [1 ]
Gouverneur, V [1 ]
机构
[1] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England
基金
英国工程与自然科学研究理事会;
关键词
cross-metathesis; desymmetrization; phosphine oxide;
D O I
10.1016/j.tet.2005.01.019
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Desymmetrization of prochiral di- and trialkenyl phosphine oxides by cross-metathesis with various olefinic partners allowed direct access to novel racemic P-stereogenic products featuring two or three different alkenyl groups. The excellent control of product selectivity and E/Z selectivity allowed the preparation of desymmetrized products in good yields from readily available precursors. These are the first examples of desymmetrization of prochiral substrates by direct cross-metathesis. (C) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2395 / 2400
页数:6
相关论文
共 28 条
[1]  
[Anonymous], 1972, ORGANIC PHOSPHORUS C
[2]   Cross-metathesis, a versatile synthetic methodology for the construction of alkenyl phosphine oxides and bis-phosphine oxides [J].
Bisaro, F ;
Gouverneur, V .
TETRAHEDRON LETTERS, 2003, 44 (38) :7133-7135
[3]   A general model for selectivity in olefin cross metathesis [J].
Chatterjee, AK ;
Choi, TL ;
Sanders, DP ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) :11360-11370
[4]   Synthesis of functionalized olefins by cross and ring-closing metatheses [J].
Chatterjee, AK ;
Morgan, JP ;
Scholl, M ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (15) :3783-3784
[5]   Synthesis of trisubstituted alkenes via olefin cross-metathesis [J].
Chatterjee, AK ;
Grubbs, RH .
ORGANIC LETTERS, 1999, 1 (11) :1751-1753
[6]   Recent developments in olefin cross-metathesis [J].
Connon, SJ ;
Blechert, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (17) :1900-1923
[7]   Synthesis of substituted P-stereogenic vinylphosphine oxides by olefin cross-metathesis [J].
Demchuk, OM ;
Pietrusiewicz, KM ;
Michrowska, A ;
Grela, K .
ORGANIC LETTERS, 2003, 5 (18) :3217-3220
[8]  
Gibson SE, 1998, TOP ORGANOMETAL CHEM, V1, P155
[9]  
GNON JF, 1995, TETRAHEDRON LETT, V36, P4421
[10]  
GOLDBERG SD, 2002, 224 ACS NAT M BOST M