Asymmetric synthesis of anti-1,2-amino alcohols via the Borono-Mannich reaction:: A formal synthesis of (-)-swainsonine

被引：101

作者：

Au, Christopher W. G. ^{[1
]}

Pyne, Stephen G. ^{[1
]}

机构：

[1] Univ Wollongong, Dept Chem, Wollongong, NSW 2522, Australia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 18期

关键词：

D O I：

10.1021/jo0610661

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral alpha-hydroxy aldehydes generated in situ by the ADH reaction of vinyl sulfones undergo a borono-Mannich reaction with, beta-styrenyl boronic acid and primary amines to give anti-1,2-amino alcohols in high enantiomeric purities (83-95% ee). This new method allows much more rapid access to these valuable chiral building blocks that has been used in a short formal synthesis ( 10 synthetic steps from 4-penten-1-ol) of (-)- swainsonine.

引用

页码：7097 / 7099

页数：3

共 27 条

[1] A CONVENIENT ASYMMETRIC-SYNTHESIS OF ANTI-BETA-AMINO ALCOHOLS - AN X-RAY CRYSTALLOGRAPHIC STUDY OF (4R)-2,2-DIMETHYL-4-[(2S)-(DIPHENYLMETHYLENEAMINO)-(1S)-HYDROXY-3-BUTEN-1-YL]-1,3-DIOXOLANE [J].

BARRETT, AGM ;

SEEFELD, MA ;

WILLIAMS, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (09) :1053-1054

[2] A new approach to (-)-swainsonine by ruthenium-catalyzed ring rearrangement [J].

Buschmann, N ;

Rückert, A ;

Blechert, S .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (12) :4325-4329

[3] SELECTIVE REACTIONS USING N-(TERT-BUTOXYCARBONYL)-2-(TERT-BUTYLDIMETHYLSILOXY)PYRROLE - CONCISE ASYMMETRIC SYNTHESES OF (+)-1-DEOXY-8-EPI-CASTANOSPERMINE AND ITS ENANTIOMER [J].

CASIRAGHI, G ;

ULGHERI, F ;

SPANU, P ;

RASSU, G ;

PINNA, L ;

FAVA, GG ;

FERRARI, MB ;

PELOSI, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (23) :2991-2997

[4] Synthesis of putative uniflorine A [J].

Davis, AS ;

Pyne, SG ;

Skelton, BW ;

White, AH .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (09) :3139-3143

[5] Synthetic methods for the stereoisomers of swainsonine and its analogues [J].

El Nemr, A .

TETRAHEDRON, 2000, 56 (44) :8579-8629

[6] Asymmetric dihydroxylation of vinyl sulfones:: routes to enantioenriched α-hydroxyaldehydes and the enantioselective syntheses of furan-2(5H)-ones [J].

Evans, P ;

Leffray, M .

TETRAHEDRON, 2003, 59 (40) :7973-7981

[7]

GELA K, 2001, TETRAHEDRON LETT, V42, P6425

[8] De novo asymmetric synthesis of D- and L-swainsonine [J].

Guo, HB ;

O'Doherty, GA .

ORGANIC LETTERS, 2006, 8 (08) :1609-1612

[9] AN EFFICIENT ROUTE TO A KEY A-RING SYNTHON FOR 1-ALPHA,25-DIHYDROXYVITAMIN D-3 AND ITS ANALOGS [J].

HATAKEYAMA, S ;

IRIE, H ;

SHINTANI, T ;

NOGUCHI, Y ;

YAMADA, H ;

NISHIZAWA, M .

TETRAHEDRON, 1994, 50 (47) :13369-13376

[10] Asymmetric synthesis of (-)-swainsonine [J].

Lindsay, KB ;

Pyne, SG .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2004, 57 (07) :669-672

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