The complete characterization of a rhodium Lewis acid-dipolarophile complex as an intermediate for the enantioselective catalytic 1,3-dipolar cycloaddition of C,N-diphenylnitrone to methacrolein

被引：81

作者：

Carmona, D ^{[1
]}

Lamata, MP

Viguri, F

Rodríguez, R

Oro, LA

Balana, AI

Lahoz, FJ

Tejero, T

Merino, P

Franco, S

Montesa, I

机构：

[1] Univ Zaragoza, Dept Quim Inorgan, Consejo Super Invest Cient, Inst Ciencia Mat Aragon, E-50009 Zaragoza, Spain

[2] Univ Zaragoza, Dept Quim Organ, Consejo Super Invest Cient, Inst Ciencia Mat Aragon, E-50009 Zaragoza, Spain

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 09期

关键词：

D O I：

10.1021/ja031995z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The 1,3-dipolar cycloaddition reaction of C,N-diphenylnitrone with methacrolein is efficiently catalyzed by the rhodium diphosphine compound (SRh,RC)-[(η5-C5Me5)Rh(R-Prophos)(H2O)](SbF6)2 [R-Prophos = (R)-(+)-1,2-bis(diphenylphosphino)-propane, 1·SbF6]; the asymmetric catalytic process occurs with reversal of regioselectivity, perfect endo selectivity, and up to 92% ee. The complete (NMR and X-ray analysis) characterization of the involved intermediate (SRh,RC)-[(η5-C5Me5)Rh(R-Prophos)(methacrolein)](SbF6)2 (7·SbF6) allows us to interpret the observed selectivity. Copyright © 2004 American Chemical Society.

引用

页码：2716 / 2717

页数：2

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