RECENT ADVANCES IN THE BORON ROUTE TO ASYMMETRIC-SYNTHESIS

被引:52
作者
BROWN, HC
RAMACHANDRAN, PV
机构
[1] H. C. Brown and R. B. Wetherill Laboratories of Chemistry, Purdue University, West Lafayette
基金
美国国家卫生研究院; 美国国家科学基金会;
关键词
D O I
10.1351/pac199466020201
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chiral organoboranes, readily available via asymmetric hydroboration or the Matteson asymmetric homologation reaction, have been successfully utilized for a general asymmetric synthesis of pure enantiomers. The recent continued successes achieved in our three-pronged approach to asymmetric synthesis - (1) asymmetric hydroboration, (2) asymmetric reduction, and (3) asymmetric allyl- and crotylboration, coupled with developments in asymmetric homologation, reveal the broad scope of these methodologies for the synthesis of stereoisomers in purities approaching 100 % ee.
引用
收藏
页码:201 / 212
页数:12
相关论文
共 59 条
[11]   CHIRAL SYNTHESIS VIA ORGANOBORANES .24. B-ALLYLBIS(2-ISOCARANYL)BORANE AS A SUPERIOR REAGENT FOR THE ASYMMETRIC ALLYLBORATION OF ALDEHYDES [J].
BROWN, HC ;
RANDAD, RS ;
BHAT, KS ;
ZAIDLEWICZ, M ;
RACHERLA, US .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (06) :2389-2392
[12]   SELECTIVE REDUCTIONS .40. A CRITICAL-EXAMINATION OF THE RELATIVE EFFECTIVENESS OF VARIOUS REDUCING AGENTS FOR THE ASYMMETRIC REDUCTION OF DIFFERENT CLASSES OF KETONES [J].
BROWN, HC ;
PARK, WS ;
CHO, BT ;
RAMACHANDRAN, PV .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (24) :5406-5412
[15]   HYDROBORATION .61. DIISOPINOCAMPHEYLBORANE OF HIGH OPTICAL PURITY - IMPROVED PREPARATION AND ASYMMETRIC HYDROBORATION OF REPRESENTATIVE CIS-DISUBSTITUTED ALKENES [J].
BROWN, HC ;
DESAI, MC ;
JADHAV, PK .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (26) :5065-5069
[16]   ASYMMETRIC REDUCTION WITH CHIRAL ORGANOBORANES BASED ON ALPHA-PINENE [J].
BROWN, HC ;
RAMACHANDRAN, PV .
ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (01) :16-24
[17]   SELECTIVE REDUCTIONS .37. ASYMMETRIC REDUCTION OF PROCHIRAL KETONES WITH B-(3-PINANYL)-9-BORABICYCLO[3.3.1]NONANE [J].
BROWN, HC ;
PAI, GG .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1384-1394
[19]  
BROWN HC, 1961, J AM CHEM SOC, V83, P486, DOI 10.1021/ja01463a055
[20]   HYDROBORATION .62. MONOISOPINOCAMPHEYLBORANE, AN EXCELLENT CHIRAL HYDROBORATING AGENT FOR TRANS-DISUBSTITUTED AND TRISUBSTITUTED ALKENES - EVIDENCE FOR A STRONG STERIC DEPENDENCE IN SUCH ASYMMETRIC HYDROBORATIONS [J].
BROWN, HC ;
JADHAV, PK ;
MANDAL, AK .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (26) :5074-5083