N-trityl-aziridinyl(diphenyl)methanol as an effective catalyst in the enantioselective addition of diethylzinc to aldehydes

被引：42

作者：

Lawrence, CF ^{[1
]}

Nayak, SK ^{[1
]}

Thijs, L ^{[1
]}

Zwanenburg, B ^{[1
]}

机构：

[1] Catholic Univ Nijmegen, NSR, Inst Mol Struct Design & Synthesis, Dept Organ Chem, NL-6525 ED Nijmegen, Netherlands

来源：

SYNLETT | 1999年 / 10期

关键词：

aziridinylmethanol; catalysis; enantioselective; dialkylzinc and aldehyde;

D O I：

10.1055/s-1999-3169

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

High levels of enantioselectivity have been achieved in the diethylzinc addition to both aromatic and aliphatic aldehydes, employing N-trityl-aziridinyl(diphenyl)methanol as the chiral catalyst. The R- and S-antipodes of the catalyst can readily be prepared from D- acid L-serine, respectively.

引用

页码：1571 / 1572

页数：2

共 16 条

[1] 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

[2] CATALYTIC ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES - SYNTHESIS AND APPLICATION OF A NEW CYCLIC CATALYST [J].

BEHNEN, W ;

MEHLER, T ;

MARTENS, J .

TETRAHEDRON-ASYMMETRY, 1993, 4 (07) :1413-1416

[3] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[4] CATALYTIC ASYMMETRIC INDUCTION - HIGHLY ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALDEHYDES [J].

KITAMURA, M ;

SUGA, S ;

KAWAI, K ;

NOYORI, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) :6071-6072

[5] Baylis-Hillman reaction of N-trityl aziridine-2-(S)-carboxaldehyde [J].

Nayak, SK ;

Thijs, L ;

Zwanenburg, B .

TETRAHEDRON LETTERS, 1999, 40 (05) :981-984

[6]

Nayak SK, 1998, SYNLETT, P1187

[7] Highly efficient synthesis of enantiomerically pure (S)-2-amino-1,2,2-triphenylethanol.: Development of a new family of ligands for the highly enantioselective catalytic ethylation of aldehydes [J].

Reddy, KS ;

Solà, L ;

Moyano, A ;

Pericàs, MA ;

Riera, A .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11) :3969-3974

[8] ENANTIOSELECTIVE ADDITION OF ORGANOZINC REAGENTS TO ALDEHYDES [J].

SOAI, K ;

NIWA, S .

CHEMICAL REVIEWS, 1992, 92 (05) :833-856

[9] A NEW CHIRAL CATALYST FOR THE HIGHLY ENANTIOSELECTIVE ADDITION OF DIALKYLZINC REAGENTS TO ALIPHATIC-ALDEHYDES [J].

SOAI, K ;

YOKOYAMA, S ;

EBIHARA, K ;

HAYASAKA, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (22) :1690-1691

[10] CATALYTIC ASYMMETRIC INDUCTION - HIGHLY ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALDEHYDES USING CHIRAL PYRROLIDINYLMETHANOLS AND THEIR METAL-SALTS [J].

SOAI, K ;

OOKAWA, A ;

KABA, T ;

OGAWA, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (23) :7111-7115

← 1 2 →