Unexpected 1,2 syn diastereoselectivity in the three-component 'aza Sakurai-Hosomi' reaction

被引：19

作者：

Ella-Menye, JR ^{[1
]}

Dobbs, W ^{[1
]}

Billet, M ^{[1
]}

Klotz, P ^{[1
]}

Mann, A ^{[1
]}

机构：

[1] Fac Pharm, UMR 7081, Lab Pharmacochim Commun Cellulaire, F-67401 Illkirch Graffenstaden, France

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 11期

关键词：

Sakurai-Hosomi reaction; three-component reaction; allylsilane; homoallylamine; diastereoselectivity;

D O I：

10.1016/j.tetlet.2005.01.077

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The three-component 'aza Sakurai-Hosomi' reaction performed on (+/-) O-protected mandelic aldehydes provided the unexpected syn hydroxy homoallylamines 2 and 2d as the major adducts. An intramolecular chelated transition state via a hydrogen bond is proposed to explain this 1,2 syn diastereoselectivity. (C) 2005 Elsevier Ltd. All rights reserved.

引用

页码：1897 / 1900

页数：4

共 19 条

[1] Stereoselective synthesis of tetrahydrofurans via formal [3+2]-cycloaddition of aldehydes and allylsilanes. Formal total synthesis of the muscarine alkaloids (-)-allomuscarine and (+)-epimuscarine [J].

Angle, SR ;

El-Said, NA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (14) :3608-3613

[2] A convenient procedure for the preparation of α-aminoallenes using a three-component reaction of aldehyde, carbamate and propargylsilane [J].

Billet, M ;

Schoenfelder, A ;

Klotz, P ;

Mann, A .

TETRAHEDRON LETTERS, 2002, 43 (08) :1453-1456

[3] Syn diastereoselectivity in the synthesis of homoallylamine using crotylsilane in the three-component reaction [J].

Billet, M ;

Klotz, P ;

Mann, A .

TETRAHEDRON LETTERS, 2001, 42 (04) :631-634

[4] PREPARATION OF 1,2 AMINOLS FROM CYANOHYDRINS VIA N-DIISOBUTYLALUMINIUM IMINES [J].

CAINELLI, G ;

PANUNZIO, M ;

CONTENTO, M ;

GIACOMINI, D ;

MEZZINA, E ;

GIOVAGNOLI, D .

TETRAHEDRON, 1993, 49 (18) :3809-3826

[5] INTRAMOLECULAR HYDROGEN-BONDING CATALYSIS OF ESTER AMINOLYSIS IN ACETONITRILE [J].

CIUFFARIN, E ;

LOI, A ;

ISOLA, M ;

LUPETTI, A ;

SAGRAMORA, L ;

SENATORE, L .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (07) :1047-1051

[6] A stereochemical model for merged 1,2- and 1,3-asymmetric induction in diastereoselective Mukaiyama aldol addition reactions and related processes [J].

Evans, DA ;

Dart, MJ ;

Duffy, JL ;

Yang, MG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (18) :4322-4343

[7] Stereochemical control in organic synthesis using silicon-containing compounds [J].

Fleming, I ;

Barbero, A ;

Walter, D .

CHEMICAL REVIEWS, 1997, 97 (06) :2063-2192

[8] A NOVEL BF(3)CENTER-DOT-OET(2)-CATALYZED [3+2] ANNULATION OF N-CBZ-ALPHA-AMINO ALDEHYDES WITH ALLYLTRIMETHYLSILANE - HIGHLY STEREOSELECTIVE SYNTHESIS OF CIS-2,3,5-TRISUBSTITUTED PYRROLIDINES [J].

KIYOOKA, S ;

SHIOMI, Y ;

KIRA, H ;

KANEKO, Y ;

TANIMORI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (08) :1958-1960

[9] A STEREOSELECTIVE SYNTHESIS OF THE (2R,3S)-3-AMINO-2-HYDROXYBUTYRIC AND (2S,3R)-3-AMINO-2-HYDROXYBUTYRIC ACID-DERIVATIVES, THE KEY COMPONENTS OF A RENIN INHIBITOR AND BESTATIN [J].

KOBAYASHI, Y ;

TAKEMOTO, Y ;

KAMIJO, T ;

HARADA, H ;

ITO, Y ;

TERASHIMA, S .

TETRAHEDRON, 1992, 48 (10) :1853-1868

[10] Synthesis of homoallylic amines via N-acyliminium ion reactions on solid support [J].

Meester, WJN ;

Rutjes, FPJT ;

Hermkens, PHH ;

Hiemstra, H .

TETRAHEDRON LETTERS, 1999, 40 (08) :1601-1604

← 1 2 →