Asymmetry in the boronic acid Mannich reaction: Diastereocontrolled addition to chiral iminium species derived from aldehydes and (S)-5-phenylmorpholin-2-one

被引：47

作者：

Harwood, LM

Currie, GS

Drew, MGB

Luke, RWA

机构：

[1] UNIV OXFORD,DYSON PERRINS LAB,OXFORD OX1 3QY,ENGLAND

[2] ZENECA PHARMACEUT,MACCLESFIELD SK10 4TG,CHESHIRE,ENGLAND

来源：

CHEMICAL COMMUNICATIONS | 1996年 / 16期

关键词：

D O I：

10.1039/cc9960001953

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(S)-5-Phenylmorpholin-2-one dagger and a range of aliphatic aldehydes form chiral iminium. intermediates which undergo diastereoselective Mannich reactions with 2-furylboronic acid, Single crystal X-ray analysis of methylated derivative 4 derived from. major adduct 2g confirms the stereochemical course of the reaction.

引用

收藏

页码：1953 / 1954

页数：2

相关论文

共 17 条

[1] DEVELOPMENT OF CHIRAL STABILIZED AZOMETHINE YLIDES - A CHIRAL MEMORY RELAY SYSTEM [J].

ANSLOW, AS ;

HARWOOD, LM ;

PHILLIPS, H ;

WATKIN, D ;

WONG, LF .

TETRAHEDRON-ASYMMETRY, 1991, 2 (12) :1343-1358

[2] ENANTIOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACID DERIVATIVES VIA THE STEREOSELECTIVE ALKYLATION OF A HOMOCHIRAL GLYCINE ENOLATE SYNTHON [J].

DELLARIA, JF ;

SANTARSIERO, BD .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (16) :3916-3926

[3]

DONDONI A, 1994, SYNTHESIS-STUTTGART, P1450

[4] ASYMMETRIC CYCLOADDITIONS OF ALDEHYDES TO STABILIZED AZOMETHINE YLIDS - ENANTIOCONTROLLED CONSTRUCTION OF BETA-HYDROXY-ALPHA-AMINO ACID-DERIVATIVES [J].

HARWOOD, LM ;

MACRO, J ;

WATKIN, D ;

WILLIAMS, CE ;

WONG, LF .

TETRAHEDRON-ASYMMETRY, 1992, 3 (09) :1127-1130

[5] ENANTIOCONTROLLED CONSTRUCTION OF BICYCLIC PROLINE DERIVATIVES VIA ONE-POT GENERATION AND INTRAMOLECULAR TRAPPING OF CHIRAL STABILIZED AZOMETHINE YLIDS [J].

HARWOOD, LM ;

LILLEY, IA .

TETRAHEDRON LETTERS, 1993, 34 (03) :537-540

[6] TANDEM GENERATION AND INTRAMOLECULAR TRAPPING OF CHIRAL STABILIZED AZOMETHINE YLIDES WITH ALKYNE DIPOLAROPHILES [J].

HARWOOD, LM ;

KITCHEN, LC .

TETRAHEDRON LETTERS, 1993, 34 (41) :6603-6606

[7] SYNTHESIS OF CARBOXYLATED PYRROLIDINE DERIVATIVES VIA 1,3-DIPOLAR CYCLOADDITIONS OF HOMOCHIRAL DOUBLE-STABILIZED E-AZOMETHINE YLIDS [J].

HARWOOD, LM ;

LILLEY, IA .

TETRAHEDRON-ASYMMETRY, 1995, 6 (07) :1557-1560

[8] EVALUATION OF SINGLE-CRYSTAL X-RAY-DIFFRACTION DATA FROM A POSITION-SENSITIVE DETECTOR [J].

KABSCH, W .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1988, 21 (06) :916-924

[9]

MANAGE A, UNPUB

[10] THE BORONIC ACID MANNICH REACTION - A NEW METHOD FOR THE SYNTHESIS OF GEOMETRICALLY PURE ALLYLAMINES [J].

PETASIS, NA ;

AKRITOPOULOU, I .

TETRAHEDRON LETTERS, 1993, 34 (04) :583-586