Asymmetric Synthesis of α-Branched Allylic Amines by the Rh(I)-Catalyzed Addition of Alkenyltrifluoroborates to N-tert-Butanesulfinyl Aldimines

被引：68

作者：

Brak, Katrien ^{[1
]}

Ellman, Jonathan A. ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 11期

关键词：

RH-CATALYZED ARYLATION; ARYLBORONIC ACIDS; ORGANOBORONIC ACIDS; IMINES; TOSYLARYLIMINES; SULFINIMINES; CHEMISTRY; REAGENTS; ALCOHOLS; HYDROGEN;

D O I：

10.1021/ja9002603

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first Rh(I)-catalyzed addition of alkenylboron reagents to imines is described. The Rh(I)-catalyzed addition of potassium alkenyltrifluoroborate salts to both aromatic and aliphatic N-tert-butanesulfinyl aldimines proceeds in good yields (up to 97%) and with very high diastereoselectivities (95:5 to >99:1). This new method enables the general and efficient asymmetric synthesis of the important class of alpha-branched allylic amines from readily available and stable starting materials.

引用

页码：3850 / +

页数：3

共 35 条

[1] Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity [J].

Anderson, CE ;

Overman, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (41) :12412-12413

[2] A room-temperature protocol for the rhodium(I)-catalyzed addition of arylboron compounds to sulfinimines [J].

Bolshan, Y ;

Batey, RA .

ORGANIC LETTERS, 2005, 7 (08) :1481-1484

[3] Total synthesis of (+)-aloperine. Use of a nitrogen-bound silicon tether in an intramolecular Diels-Alder reaction [J].

Brosius, AD ;

Overman, LE ;

Schwink, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (04) :700-709

[4] Asymmetric synthesis of chiral amines by highly diastereoselective 1,2-additions of organometallic reagents to N-tert-butanesulfinyl imines [J].

Cogan, DA ;

Liu, GC ;

Ellman, J .

TETRAHEDRON, 1999, 55 (29) :8883-8904

[5] Potassium organotrifluoroborates: New perspectives in organic synthesis [J].

Darses, Sylvain ;

Genet, Jean-Pierre .

CHEMICAL REVIEWS, 2008, 108 (01) :288-325

[6]

DENMARK SE, 2000, J ORG CHEM, V65, P58753

[7] Enantioselective Rh-catalyzed arylation of N-tosylarylimines with arylboronic acids [J].

Duan, Hai-Feng ;

Jia, Yi-Xia ;

Wang, Li-Xin ;

Zhou, Qi-Lin .

ORGANIC LETTERS, 2006, 8 (12) :2567-2569

[8] N-tert-Butanesulfinyl imines:: Versatile intermediates for the asymmetric synthesis of amines [J].

Ellman, JA ;

Owens, TD ;

Tang, TP .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (11) :984-995

[9]

GROSSMAN RB, 1991, J AM CHEM SOC, V113, P23212

[10] Catalytic cycle of rhodium-catalyzed asymmetric 1,4-addition of organoboronic acids.: Arylrhodium, oxa-π-allylrhodium, and hydroxorhodium intermediates [J].

Hayashi, T ;

Takahashi, M ;

Takaya, Y ;

Ogasawara, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (18) :5052-5058

← 1 2 3 4 →