Diastereoselective synthesis of 1,2-diphenyl-1,2-diaminoethanes by Yb(OTf)3 accelerated reductive coupling of imines

被引：51
作者：
Annunziata, R
Benaglia, M
Cinquini, M
Cozzi, F
Raimondi, L
机构：
[1] Univ Milan, Ctr CNR, I-20133 Milan, Italy
[2] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
来源：
TETRAHEDRON LETTERS | 1998年 / 39卷 / 20期
关键词：
diamines; reduction; stereoselection; lanthanides;
D O I：
10.1016/S0040-4039(98)00484-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
New reaction protocols have been established to perform the reductive coupling of N-benzyl benzaldimines to 1,2-diphenyl-1,2-diaminoethanes in mild, stereoselective, and catalytic conditions by the use of SmI2 and Yb(OTf)(3). (C) 1998 Elsevier Science Ltd. All rights reserved.
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页码：3333 / 3336
页数：4
相关论文
共 35 条
[1]   CHIRAL DIAMINES FOR A NEW PROTOCOL TO DETERMINE THE ENANTIOMERIC COMPOSITION OF ALCOHOLS, THIOLS, AND AMINES BY P-31, H-1, C-13, AND F-19 NMR [J].
ALEXAKIS, A ;
FRUTOS, JC ;
MUTTI, S ;
MANGENEY, P .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3326-3334
[2]   A new multicomponent synthesis of 1,2,3,4-tetrahydroquinolines [J].
Annunziata, R ;
Cinquini, M ;
Cozzi, F ;
Molteni, V ;
Schupp, O .
TETRAHEDRON, 1997, 53 (28) :9715-9726
[3]   Yb(OTf)(3)-Catalyzed one-pot synthesis of beta-lactams from silyl ketene thioacetals by a two- or a three-component reaction [J].
Annunziata, R ;
Cinquini, M ;
Cozzi, F ;
Molteni, V ;
Schupp, O .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :8293-8296
[4]   SIMPLE SYNTHESIS OF A C-2 SYMMETRICAL VICINAL DIAMINE - HIGHLY DIASTEREOSELECTIVE GRIGNARD ADDITION TO A CHIRAL BIS-IMINE [J].
BAMBRIDGE, K ;
BEGLEY, MJ ;
SIMPKINS, NS .
TETRAHEDRON LETTERS, 1994, 35 (20) :3391-3394
[5]  
BARUAH B, 1995, TETRAHEDRON LETT, V36, P6747, DOI 10.1016/0040-4039(95)01331-B
[6]   SCOPE AND LIMITATIONS OF THE REDUCTIVE COUPLING OF AROMATIC ALDIMINE DERIVATIVES WITH FORMATION OF 1,2-DIARYLETHYLENEDIAMINE UNITS, USING LOW-VALENT TITANIUM REAGENTS [J].
BETSCHART, C ;
SCHMIDT, B ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1988, 71 (08) :1999-2021
[7]   ZIRCONOCENE COMPLEXES OF IMINES - GENERAL-SYNTHESIS, STRUCTURE, REACTIVITY, AND INSITU GENERATION TO PREPARE GEOMETRICALLY PURE ALLYLIC AMINES [J].
BUCHWALD, SL ;
WATSON, BT ;
WANNAMAKER, MW ;
DEWAN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4486-4494
[8]   ASYMMETRIC-SYNTHESIS USING HOMOCHIRAL LITHIUM AMIDE BASES [J].
COX, PJ ;
SIMPKINS, NS .
TETRAHEDRON-ASYMMETRY, 1991, 2 (01) :1-26
[9]  
Enders D, 1997, B SOC CHIM FR, V134, P299
[10]  
Enders D, 1996, SYNTHESIS-STUTTGART, P1443
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