Bromo-boronolactonization of olefins

被引：45

作者：

Falck, JR

Bondlela, M

Venkataraman, SK

Srinivas, D

机构：

[1] Univ Texas, SW Med Ctr, Dept Biochem, Dallas, TX 75390 USA

[2] Univ Texas, SW Med Ctr, Dept Pharmacol, Dallas, TX 75390 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 21期

关键词：

D O I：

10.1021/jo015838z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Exposure of a variety of mono- and disubstituted ortho-alkenylarylboronic acids to NBS in THF/ H2O under neutral conditions affords bromo-boronolactones, in some instances, with exceptional regiocontrol. The adducts, analogous to those formed by carboxylic acids, are shown to be useful synthetic intermediates.

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页码：7148 / 7150

页数：3

相关论文

共 22 条

[1] 3-HYDROXYLEUKOTRIENE B-4(3-OH-LTB(4)) - TOTAL SYNTHESIS AND STEREOCHEMICAL ASSIGNMENT [J].

BHATT, RK ;

CHAUHAN, K ;

WHEELAN, P ;

MURPHY, RC ;

FALCK, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (12) :5050-5056

[2]

CARDILLO G, 1996, STEREOSELECTIVE SYNT, V8

[3] ARYLBORONIC ACIDS - A MEDIUM-SIZE RING CONTAINING BORONIC ESTER GROUPS [J].

CUMMINGS, WM ;

COX, CH ;

SNYDER, HR .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (06) :1669-&

[4] BROMOHYDRIN FORMATION IN AQUEOUS DIMETHYL SULPHOXIDE - ELECTRONIC AND STERIC EFFECTS [J].

DALTON, DR ;

DUTTA, VP .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1971, (01) :85-&

[5]

DOWLE MD, 1979, CHEM SOC REV, P171

[6] BROMOHYDRINS FROM OLEFINS AND N-BROMOSUCCINIMIDE IN WATER [J].

GUSS, CO ;

ROSENTHAL, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (09) :2549-2549

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

Harwood, LM ;

Currie, GS ;

Drew, MGB ;

Luke, RWA .

CHEMICAL COMMUNICATIONS, 1996, (16) :1953-1954

[8]

HAYNES RR, 1964, J ORG CHEM, V29, P3239

[9] Synthesis of arylboronates via the palladium(O)-catalyzed cross-coupling reaction of tetra(alkoxo)diborons with aryl triflates [J].

Ishiyama, T ;

Itoh, Y ;

Kitano, T ;

Miyaura, N .

TETRAHEDRON LETTERS, 1997, 38 (19) :3447-3450

[10] PALLADIUM(O)-CATALYZED CROSS-COUPLING REACTION OF ALKOXYDIBORON WITH HALOARENES - A DIRECT PROCEDURE FOR ARYLBORONIC ESTERS [J].

ISHIYAMA, T ;

MURATA, M ;

MIYAURA, N .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (23) :7508-7510