ADDITION OF DIETHYLZINC TO ARYL ALDEHYDES CATALYZED BY (1S,3S)-N,NI-BIS[BENZYL]-1,3-DIPHENYL-1,3-PROPANEDIAMINE AND ITS DILITHIUM SALT - A MECHANISTIC RATIONALE INVESTIGATION

被引：47

作者：

PINI, D ^{[1
]}

MASTANTUONO, A ^{[1
]}

UCCELLOBARRETTA, G ^{[1
]}

IULIANO, A ^{[1
]}

SALVADORI, P ^{[1
]}

机构：

[1] UNIV PISA,CNR,CTR STUDI MACROMOLEC STEREORDINATE & OTTICAMENTE ATT,DIPARTIMENTO CHIM & CHIM IND,I-56126 PISA,ITALY

来源：

TETRAHEDRON | 1993年 / 49卷 / 42期

关键词：

D O I：

10.1016/S0040-4020(01)80230-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N,N1-bis-benzyl substituted 1,3-diamine 1a, synthesized in high optical purity, and the corresponding dilithium salt 1b are used, for the first time, as chiral catalysts in the addition of ZnEt2 to aromatic aldehydes. Both 1a and 1b are able to promote the reaction but the products obtained exhibited low enantiomeric excesses. By H-1 NMR and UV-CD investigation, experimental evidences about the structure of some reaction intermediates have been gained: reaction pathway consistent with spectroscopic data, chemical and stereochemical results could be postulated.

引用

页码：9613 / 9624

页数：12

共 12 条

[1] ORGANOMETALLIC COMPOUNDS .3. ACIDOLYSIS OF SOME SYMMETRICAL AND UNSYMMETRICAL-DIAIKYLZINCS BY PRIMARY AMINES [J].