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
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.
引用
收藏
页码:7148 / 7150
页数:3
相关论文
共 22 条
[11]   PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS [J].
MIYAURA, N ;
SUZUKI, A .
CHEMICAL REVIEWS, 1995, 95 (07) :2457-2483
[12]  
NAGATA W, 1979, SYNTHESIS-STUTTGART, P365
[13]  
Sakai M, 1998, ANGEW CHEM INT EDIT, V37, P3279, DOI 10.1002/(SICI)1521-3773(19981217)37:23<3279::AID-ANIE3279>3.0.CO
[14]  
2-M
[15]  
Siebert W., 1997, ADV BORON CHEM
[16]   An improved synthesis of iodohydrins from alkenes [J].
Smietana, M ;
Gouverneur, V ;
Mioskowski, C .
TETRAHEDRON LETTERS, 2000, 41 (02) :193-195
[17]   CYCLIC BENZENEBORONATE ESTERS [J].
SUGIHARA, JM ;
BOWMAN, CM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (10) :2443-2446
[18]  
TORSELL K, 1964, PROGR BORON CHEM, V1, pCH9
[19]  
TORSSELL K, 1957, ARK KEMI, V10, P507
[20]  
TORSSELL K, 1957, ARK KEMI, V10, P473