Catalytic enantioselective amination of enolsilanes using C2-symmetric copper(II) complexes as chiral Lewis acids

被引：171

作者：

Evans, DA ^{[1
]}

Johnson, DS ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 04期

关键词：

D O I：

10.1021/ol990113r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] [Cu(S,S)-t-Bu-box](OTf)(2) (1) catalyzes the enantioselective amination of enolsilanes with azodicarboxylate derivatives. Isomerically pure enolsilanes of aryl ketones, acylpyrroles, and thioesters added to the azo imide in greater than 95% ee. The use of an alcohol additive was critical to achieving catalyst turnover.

引用

页码：595 / 598

页数：4

共 40 条

[21] ASYMMETRIC ELECTROPHILIC AMINATION - SYNTHESIS OF ALPHA-AMINO AND ALPHA-HYDRAZINO ACIDS WITH HIGH OPTICAL PURITY [J].

GENNARI, C ;

COLOMBO, L ;

BERTOLINI, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) :6394-6395

[22]

Greck C, 1997, SYNLETT, P741

[23]

Grehn L, 1998, SYNTHESIS-STUTTGART, P1817

[24] KINETICS OF THE REACTIONS OF PHENYLKETENE DIMETHYL ACETAL WITH AZOCARBOXYLATE ESTERS [J].

HALL, JH ;

WOJCIECHOWSKA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 44 (01) :38-41

[25] REACTIONS OF KETENE ACETALS, KETENE THIOACETALS, AND KETENE AMINALS WITH DIALKYL AZODICARBOXYLATE ESTERS [J].

HALL, JH ;

WOJCIECHOWSKA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (17) :3348-3353

[26] Synthesis of a chiral azodicarboxamide containing abridging binaphthyl moiety: Electrophilic amination reactions of achiral ester enolates [J].

Harris, JM ;

McDonald, R ;

Vederas, JC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (22) :2669-2674

[27] SYNTHESIS OF OPTICALLY-ACTIVE (E)-1-ALKOXYMETHOXYBUT-2-ENYL(TRIBUTYL)STANNANES - STEREOCHEMISTRY OF THEIR THERMAL-REACTIONS WITH ALDEHYDES [J].

JEPHCOTE, VJ ;

PRATT, AJ ;

THOMAS, EJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (08) :1529-1535

[28] A NEW FACILE DIASTEREOCONVERSION OF 2-AMINO ALCOHOLS INVOLVING A NOVEL CYCLOCARBAMATION [J].

KANO, S ;

YOKOMATSU, T ;

IWASAWA, H ;

SHIBUYA, S .

TETRAHEDRON LETTERS, 1987, 28 (50) :6331-6334

[29] Ribosome-mediated incorporation of hydrazinophenylalanine into modified peptide and protein analogues [J].

Killian, JA ;

Van Cleve, MD ;

Shayo, YF ;

Hecht, SM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (13) :3032-3042

[30] [4+2] CYCLO-ADDITION REACTION OF BIS (TRICHLOROETHYL) AZODICARBOXYLATE AND GLYCALS - PREPARATION OF A C1-C1 2-AMINO DISACCHARIDE [J].

LEBLANC, Y ;

FITZSIMMONS, BJ .

TETRAHEDRON LETTERS, 1989, 30 (22) :2889-2892

← 1 2 3 4 →