Diastereoselective and enantioselective Rh(l)-catalyzed additions of arylboronic acids to N-tert-butanesulfinyl and N-diphenylphosphinoyl aldimines

被引：169

作者：

Weix, DJ ^{[1
]}

Shi, YL ^{[1
]}

Ellman, JA ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Ctr New Direct Organ Synth, Berkeley, CA 94720 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 04期

关键词：

D O I：

10.1021/ja044003d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two new Rh(I)-catalyzed methods for the synthesis of chiral α-branched amines via addition of arylboronic acids to N-tert-butanesulfinyl and N-diphenylphosphinoyl imines have been developed. The syntheses are more functional group tolerant than alternative methods utilizing Grignard or organolithium reagents, and the imine activating groups used are easily removed. These methods are both high-yielding (70-97% yield) and very selective (>93:7 dr and 88-94% ee). Significantly, the N-tert-butanesulfinyl imine method works for aliphatic imines with enolizable protons. In addition, a one-pot procedure for the synthesis of N-tert-butanesulfinyl protected α-branched amines from aldehydes has been developed. Copyright © 2005 American Chemical Society.

引用

页码：1092 / 1093

页数：2

共 30 条

[1] Three-component enantioselective synthesis of propargylamines through Zr-catalyzed additions of alkyl zinc reagents to alkynylimines [J].

Akullian, LC ;

Snapper, ML ;

Hoveyda, AH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (35) :4244-4247

[2] Preparation and use of aziridino alcohols as promoters for the enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl) imines [J].

Andersson, PG ;

Guijarro, D ;

Tanner, D .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7364-7375

[3] Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].

Bloch, R .

CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438

[4] SYNTHESIS AND CHARACTERIZATION OF RH(P(CH3)3)2(CO)CH3 AND RH(P(CH3)3)2(CO)PH [J].

BOYD, SE ;

FIELD, LD ;

HAMBLEY, TW ;

PARTRIDGE, MG .

ORGANOMETALLICS, 1993, 12 (05) :1720-1724

[5] Diastereoselective synthesis of trans-ethynyl N-tert-butanesulfinylaziridines [J].

Chemla, F ;

Ferreira, F .

SYNLETT, 2004, (06) :983-986

[6] Catalytic asymmetric addition of diorganozinc reagents to N-phosphinoylalkylimines [J].

Cóté, A ;

Boezio, AA ;

Charette, AB .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5405-5410

[7] 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

[8] Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds [J].

Fagnou, K ;

Lautens, M .

CHEMICAL REVIEWS, 2003, 103 (01) :169-196

[9] Effective tuning of the arene and alkanesulfinamides for highly enantioselective synthesis of (S)-4-chlorophenylphenylmethylamine, a key intermediate for antihistamic (S)-cetirizine [J].

Han, ZX ;

Krishnamurthy, D ;

Grover, P ;

Fang, QK ;

Pflum, DA ;

Senanayake, CH .

TETRAHEDRON LETTERS, 2003, 44 (22) :4195-4197

[10] Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions [J].

Hayashi, T ;

Yamasaki, K .

CHEMICAL REVIEWS, 2003, 103 (08) :2829-2844

← 1 2 3 →