Rhodium catalysed enantioselective hydroboration of alkenylboronic esters with catecholborane

被引：29

作者：

Wiesauer, C ^{[1
]}

Weissensteiner, W ^{[1
]}

机构：

[1] UNIV VIENNA,INST ORGAN CHEM,A-1090 VIENNA,AUSTRIA

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 01期

关键词：

D O I：

10.1016/0957-4166(95)00407-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Alkenylboronic esters such as (E)-2-(2-phenylethenyl)-1,3,2-dioxaborolane were subjected to catalytic hydroboration with catecholborane and with use of neutral and cationic rhodium complexes modified by various diphosphine ligands. The resulting 1,2-diboryl intermediate was oxidised with alkaline hydrogen peroxide to give the corresponding 1,2-diol with enantioselectivities up to 79 % e.e.

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页码：5 / 8

页数：4

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共 31 条

[1] HYDROBORATION .39. 1,3,2-BENZODIOXABOROLE (CATECHOLBORANE) AS A NEW HYDROBORATION REAGENT FOR ALKENES AND ALKYNES - GENERAL SYNTHESIS OF ALKANEBORONIC AND ALKENEBORONIC ACIDS AND ESTERS VIA HYDROBORATION - DIRECTIVE EFFECTS IN HYDROBORATION OF ALKENES AND ALKYNES WITH CATECHOLBORANE [J].

BROWN, HC ;

GUPTA, SK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (18) :5249-5255

[2] CATALYTIC ASYMMETRIC HYDROBORATION WITH OXAZABOROLIDINES [J].

BROWN, JM ;

LLOYDJONES, GC .

TETRAHEDRON-ASYMMETRY, 1990, 1 (12) :869-872

[3] VINYLBORANE FORMATION IN RHODIUM-CATALYZED HYDROBORATIONS - LIGAND-FREE HOMOGENEOUS CATALYSIS [J].

BROWN, JM ;

LLOYDJONES, GC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (09) :710-712

[4] VINYLBORANE FORMATION IN RHODIUM-CATALYZED HYDROBORATION OF VINYLARENES - MECHANISM VERSUS BORANE STRUCTURE AND RELATIONSHIP TO SILATION [J].

BROWN, JM ;

LLOYDJONES, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (03) :866-878

[5] SUBSTRATE-CONTROLLED DIASTEREOSELECTIVITY IN CATALYZED AND UNCATALYZED HYDROBORATIONS OF ALLYLIC AMINE DERIVATIVES [J].

BURGESS, K ;

OHLMEYER, MJ .

TETRAHEDRON LETTERS, 1989, 30 (43) :5857-5860

[6] DIASTEREOCONTROL IN RHODIUM-CATALYZED HYDROBORATION OF CHIRAL ACYCLIC ALLYLIC ALCOHOL DERIVATIVES [J].

BURGESS, K ;

OHLMEYER, MJ .

TETRAHEDRON LETTERS, 1989, 30 (04) :395-398

[7] ENANTIOSELECTIVE HYDROBORATIONS CATALYZED BY RHODIUM(+1) COMPLEXES [J].

BURGESS, K ;

VANDERDONK, WA ;

OHLMEYER, MJ .

TETRAHEDRON-ASYMMETRY, 1991, 2 (07) :613-621

[8] SUBSTRATE-CONTROLLED DIASTEREOSELECTIVITIES IN CATALYZED AND UNCATALYZED HYDROBORATIONS OF ACYCLIC ALLYLIC ALCOHOL DERIVATIVES - SECONDARY ORBITAL EFFECTS INVOLVING D-PI-P-PI INTERACTIONS [J].

BURGESS, K ;

CASSIDY, J ;

OHLMEYER, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) :1020-1027

[9] RUTHENIUM-CATALYZED HYDROBORATIONS OF ALKENES [J].

BURGESS, K ;

JASPARS, M .

ORGANOMETALLICS, 1993, 12 (10) :4197-4200

[10] ON CATALYZED AND UNCATALYZED HYDROBORATIONS OF CHIRAL ALLYLIC ALCOHOLS AND AMINES [J].

BURGESS, K ;

OHLMEYER, MJ .

TETRAHEDRON LETTERS, 1989, 30 (43) :5861-5864

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