STEREOCONTROLLED SYNTHESIS OF HOMOALLYLIC AMINES USING PHOSPHINE OXIDES AND ISOXAZOLINES

被引：18

作者：

ARMSTRONG, SK

WARREN, S

COLLINGTON, EW

NAYLOR, A

机构：

[1] UNIV CAMBRIDGE,CHEM LAB,LENSFIELD RD,CAMBRIDGE CB2 1EW,ENGLAND

[2] GLAXO GRP RES LTD,WARE SG12 0DP,HERTS,ENGLAND

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 33期

关键词：

D O I：

10.1016/S0040-4039(00)79895-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allylic diphenylphosphine oxides (7) undergo stereoselective 1,3-dipolar cycloadditions with nitrile oxides to give DELTA-2-isoxazolines (8). These may be reduced, also stereoselectively, to delta-amino-beta-hydroxyalkyldiphenylpoxides (9). Stereospecific Witting-Horner type elimination of Ph2PO2-from amino alcohols (9) gives homoallylic amines (10) with controlled double bond geometry.

引用

页码：4171 / 4174

页数：4

共 17 条

[1] ENANTIOMERICALLY PURE SULPHINYL-4,5-DIHYDROISOXAZOLES .1. STEREOCONTROLLED SYNTHESIS OF OPTICALLY-ACTIVE BETA-KETOLS AND GAMMA-AMINO ALCOHOLS
ANNUNZIATA, R
CINQUINI, M
COZZI, F
GILARDI, A
RESTELLI, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11): : 2289 - 2292
[2] ULTRASOUND IN CYCLO-ADDITION REACTIONS - SOUND-PROMOTED DIPOLAR CYCLO-ADDITIONS OF NITRONES WITH UNACTIVATED ALKENES
BORTHAKUR, DR
SANDHU, JS
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (22) : 1444 - 1445
[3] HYDROBORATION .25. HYDROBORATION OF 3-BUTENYL DERIVATIVES CONTAINING REPRESENTATIVE SUBSTITUENTS
BROWN, HC
UNNI, MK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (11) : 2902 - +
[4] APPLICATIONS OF THE STEREOCHEMICALLY-CONTROLLED HORNER-WITTIG REACTION - SYNTHESIS OF FENICULIN, (E)-NON-6-EN-1-OL, A PHEROMONE OF THE MEDITERRANEAN FRUIT-FLY, (E)-DEC-5-EN-1-OL, AND (Z)-DEC-5-EN-1-OL, TRI-SUBSTITUTED ALKENES, AND (Z)-ALPHA-BISABOLENE
BUSS, AD
GREEVES, N
MASON, R
WARREN, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (12): : 2569 - 2577
[5] CARAMELLA P, 1984, 1 3 DIPOLAR CYCLOADD, V1, P337
[6] HORNER-WITTIG REACTIONS OF BETA-AMINOALKYL-ACYLAMINOALKYLDIPHENYLPHOSPHINE AND BETA-N-ACYLAMINOALKYLDIPHENYLPHOSPHINE OXIDES - SYNTHESIS OF N-ALLYL AMINES AND AMIDES AND 5-DIPHENYLPHOSPHINOYL-2-PHENYL-5,6-DIHYDRO-4H-1,3-OXAZINES
CAVALLA, D
CRUSE, WB
WARREN, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (09): : 1883 - 1898
[7] DANTAS TND, 1983, TETRAHEDRON, V39, P3337
[8] CHEMISTRY OF ORGANO-SILICON COMPOUNDS .205. REGIOSELECTIVE CYCLO-ADDITION REACTIONS OF ALLYLSILANES AND SILYL ENOL ETHERS WITH NITRONES AND NITRILE OXIDES - SYNTHESIS OF HOMOALLYLAMINES
HOSOMI, A
SHOJI, H
SAKURAI, H
[J]. CHEMISTRY LETTERS, 1985, (07) : 1049 - 1052
[9] STERIC MODELS FOR STEREOSELECTIVITY OF NITRILE OXIDE CYCLOADDITIONS TO CHIRAL ALKENES
HOUK, KN
DUH, HY
WU, YD
MOSES, SR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (10) : 2754 - 2755
[10] STEREOSELECTIVE ADDITION-REACTIONS OF CHIRAL N-BENZYLIDENE-PARA-TOLUENESULFINAMIDES - ASYMMETRIC SYNTHESES OF BETA-AMINO AND GAMMA-AMINO ACIDS
HUA, DH
MIAO, SW
CHEN, JS
IGUCHI, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) : 4 - 6

← 1 2 →