Diastereoselective temporary silicon-tethered ring-closing-metathesis reactions with prochiral alcohols: A new approach to long-range asymmetric induction

被引：56
作者：
Evans, PA [1 ]
Cui, B
Buffone, GP
机构：
[1] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
[2] Univ Delaware, Dept Chem & Biochem, Newark, DE 19716 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 15期
关键词：
cyclization; diastereoselectivity; medium-sized rings; metathesis; silicon;
D O I：
10.1002/anie.200250486
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A useful approach to 1,4-, 1,5-, and 1,6-stereocontrol, diastereoselective ring-closing-metathesis reactions that utilize temporary silicon tethers represent a new strategy for long-range asymmetric induction. This method facilitates the construction of cis-1,4-silaketals (n = 0, d.r. = 20:1; see scheme), whereas the extension of this concept to higher alkenyl alcohols (n = 1-4) results in a reversal of diastereoselectivity that favors formation of the trans isomer.
引用
收藏
页码：1734 / 1737
页数：4
相关论文
共 41 条
[1]   Formation of dissymmetric eight-membered silalketals by ring-closing metathesis and their conversion to spiroketals [J].
Boiteau, JG ;
Van de Weghe, P ;
Eustache, J .
TETRAHEDRON LETTERS, 2001, 42 (02) :239-242
[2]  
Burke S.D., 1999, ORG LETT, V1, P1827
[3]  
Carson M. W., 2001, ANGEW CHEM, V113, P4585
[4]  
Carson MW, 2001, ANGEW CHEM INT EDIT, V40, P4453, DOI 10.1002/1521-3773(20011203)40:23<4453::AID-ANIE4453>3.0.CO
[5]  
2-4
[6]   Efficient 1,8- and 1,9-asymmetric inductions in the Grignard reaction of δ- and ε-keto esters of 1,1′-binaphthalen-2-ols with an oligoether tether as the 2′-substituent:: application to the synthesis of (-)-malyngolide [J].
Date, M ;
Tamai, Y ;
Hattori, T ;
Takayama, H ;
Kamikubo, Y ;
Miyano, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (07) :645-653
[7]   Temporary silicon-tethered ring-closing metathesis approach to C2-symmetrical 1,4-diols:: Asymmetric synthesis of D-altritol [J].
Evans, PA ;
Murthy, VS .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (20) :6768-6769
[8]  
Fensterbank L, 1997, SYNTHESIS-STUTTGART, P813
[9]   Enantioselective synthesis of 1,5-anti- and 1,5-syn-diols using a highly diastereoselective one-pot double allylboration reaction sequence [J].
Flamme, EM ;
Roush, WR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (46) :13644-13645
[10]   THE APPLICATION OF CATALYTIC RING-CLOSING OLEFIN METATHESIS TO THE SYNTHESIS OF UNSATURATED OXYGEN HETEROCYCLES [J].
FU, GC ;
GRUBBS, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5426-5427
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