THE BORONIC ACID MANNICH REACTION - A NEW METHOD FOR THE SYNTHESIS OF GEOMETRICALLY PURE ALLYLAMINES

被引：366

作者：

PETASIS, NA

AKRITOPOULOU, I

机构：

[1] Department of Chemistry, University of Southern California, Los Angeles

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 04期

关键词：

D O I：

10.1016/S0040-4039(00)61625-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of vinyl boronic acids with the adducts of secondary amines and paraformaldehyde gives tertiary allylamines with the same geometry. This simple and practical method was used for the synthesis of geometrically pure naftifine, a potent antifungal agent.

引用

页码：583 / 586

页数：4

共 26 条

[1] TERBINAFINE - A REVIEW OF ITS PHARMACODYNAMIC AND PHARMACOKINETIC PROPERTIES, AND THERAPEUTIC POTENTIAL IN SUPERFICIAL MYCOSES
BALFOUR, JA
FAULDS, D
[J]. DRUGS, 1992, 43 (02) : 259 - 284
[2] A SIMPLE STEREOSELECTIVE SYNTHESIS OF PRIMARY ALLYLIC AMINES FROM 4-AMINO-1-AZADIENES
BARLUENGA, J
AGUILAR, E
JOGLAR, J
OLANO, B
FUSTERO, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (16) : 1132 - 1134
[3] A NOVEL ROUTE TO 1,3-DIENYL-2-BORONIC ESTERS PROVIDING SIMPLE SYNTHESES OF CONJUGATED [E,E]-DIENES AND CONJUGATED [E]-ALKENONES
BROWN, HC
BHAT, NG
IYER, RR
[J]. TETRAHEDRON LETTERS, 1991, 32 (30) : 3655 - 3658
[4] VINYLIC ORGANOBORANES .15. MERCURATION OF 2-ALKENYL-1,3,2-BENZODIOXABOROLES AND BORONIC ACIDS - A CONVENIENT STEREOSPECIFIC PROCEDURE FOR THE CONVERSION OF ALKYNES INTO (E)-1-HALO-1-ALKENES VIA MERCURIC-SALTS
BROWN, HC
LAROCK, RC
GUPTA, SK
RAJAGOPALAN, S
BHAT, NG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (26) : 6079 - 6084
[5] CATECHOLBORANE (1,3,2-BENZODIOXABOROLE) AS A NEW, GENERAL MONOHYDROBORATION REAGENT FOR ALKYNES - CONVENIENT SYNTHESIS OF ALKENEBORONIC ESTERS AND ACIDS FROM ALKYNES VIA HYDROBORATION
BROWN, HC
GUPTA, SK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (12) : 4370 - &
[6] ORGANOBORANES .37. SYNTHESIS AND PROPERTIES OF (Z)-1-ALKENYLBORONIC ESTERS
BROWN, HC
IMAI, T
[J]. ORGANOMETALLICS, 1984, 3 (09) : 1392 - 1395
[7] ZIRCONOCENE COMPLEXES OF IMINES - GENERAL-SYNTHESIS, STRUCTURE, REACTIVITY, AND INSITU GENERATION TO PREPARE GEOMETRICALLY PURE ALLYLIC AMINES
BUCHWALD, SL
WATSON, BT
WANNAMAKER, MW
DEWAN, JC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) : 4486 - 4494
[8] Cheikh R. B., 1983, SYNTHESIS-STUTTGART, P685, DOI DOI 10.1055/S-1983-30473
[9] AN EFFICIENT, PALLADIUM-CATALYZED ROUTE TO PROTECTED ALLYLIC AMINES
CONNELL, RD
REIN, T
AKERMARK, B
HELQUIST, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (16) : 3845 - 3849
[10] A SIMPLE SYNTHESIS OF PRIMARY E-ALLYLIC AMINES FROM 1-TRIBUTYLSTANNYL-3-BIS(TRIMETHYLSILYL)AMINO PROP-1-ENE
CORRIU, RJP
BOLIN, G
MOREAU, JJE
[J]. TETRAHEDRON LETTERS, 1991, 32 (33) : 4121 - 4124

← 1 2 3 →