Polystyrenes with chiral phosphoramide substituents as Lewis base catalysts for asymmetric addition of allyltrichlorosilane: enhancement of catalytic performance by polymer effect

被引：15

作者：

Oyama, T ^{[1
]}

Yoshioka, H ^{[1
]}

Tomoi, M ^{[1
]}

机构：

[1] Yokohama Natl Univ, Fac Engn, Dept Adv Mat Chem, Hodogaya Ku, Yokohama, Kanagawa 2408501, Japan

来源：

CHEMICAL COMMUNICATIONS | 2005年 / 14期

关键词：

D O I：

10.1039/b417311b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In the asymmetric addition of allyltrichlorosilane to benzaldehyde, polystyrenes with chiral phosphoramide substituents as Lewis base catalysts showed up to 2.4 times better catalytic activity and 1.4 times higher enantioselectivity than the corresponding low-molecular-weight analogues.

引用

收藏

页码：1857 / 1859

页数：3

相关论文

共 27 条

[1] A NEW REAGENT FOR THE DETERMINATION OF THE OPTICAL PURITY OF PRIMARY, SECONDARY, AND TERTIARY CHIRAL ALCOHOLS AND OF THIOLS [J].

ALEXAKIS, A ;

MUTTI, S ;

MANGENEY, P .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (04) :1224-1237

[2]

Angell RM, 1997, CHEM COMMUN, P919

[3]

[Anonymous], POLYM MAT ORGANIC SY

[4]

[Anonymous], POLYM MAT ORGANIC SY

[5] Catalytic enantioselective addition of allylic organometallic reagents to aldehydes and ketones [J].

Denmark, SE ;

Fu, JP .

CHEMICAL REVIEWS, 2003, 103 (08) :2763-2793

[6] Understanding the correlation of structure and selectivity in the chiral-phosphoramide-catalyzed enantioselective allylation reactions:: Solution and solid-state structural studies of bisphosphoramide•SnCl4 complexes [J].

Denmark, SE ;

Fu, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (08) :2208-2216

[7] Synthesis of phosphoramides for the Lewis base-catalyzed allylation and aldol addition reactions [J].

Denmark, SE ;

Su, YP ;

Nishigaichi, Y ;

Coe, DM ;

Wong, KT ;

Winter, SBD ;

Choi, JY .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (06) :1958-1967

[8] ASYMMETRIC ALLYLATION OF ALDEHYDES WITH CHIRAL LEWIS-BASES [J].

DENMARK, SE ;

COE, DM ;

PRATT, NE ;

GRIEDEL, BD .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6161-6163

[9] Catalytic, enantioselective addition of substituted allylic trichlorosilanes using a rationally-designed 2,2′-bispyrrolidine-based bisphosphoramide [J].

Denmark, SE ;

Fu, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (38) :9488-9489

[10] Catalytic enantioselective allylation with chiral Lewis bases [J].

Denmark, SE ;

Fu, JP .

CHEMICAL COMMUNICATIONS, 2003, (02) :167-170