CHIRAL SYNTHESIS VIA ORGANOBORANES .32. SYNTHESIS OF B-(CYCLOALK-2-ENYL)-DIISOPINOCAMPHEYLBORANES OF HIGH ENANTIOMERIC PURITY VIA THE ASYMMETRIC HYDROBORATION OF CYCLOALKA-1,3-DIENES - SUCCESSFUL ASYMMETRIC ALLYLBORATIONS OF ALDEHYDES WITH B-(CYCLOALK-2-ENYL)DIISOPINOCAMPHEYLBORANES

被引：22

作者：

BROWN, HC ^{[1
]}

BHAT, KS ^{[1
]}

JADHAV, PK ^{[1
]}

机构：

[1] PURDUE UNIV,RICHARD B WETHERILL LAB CHEM,W LAFAYETTE,IN 47907

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 11期

关键词：

D O I：

10.1039/p19910002633

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hydroboration of cycloalka-1,3-dienes (C(n)H2n-4, n = 6, 7 and 8) with diisopinocampheylborane ((d)lpc2BH or 'lpc2BH) at -25-degrees-C provides highly enantiomerically pure B-(cycloalk-2-enyl)diisopinocampheylboranes, (l or d)lpc2BCnH2n-3 (greater-than-or-equal-to 93% ee). Surprisingly, these allylic borane derivatives retain their stereochemical integrity at -25-degrees-C although such compounds are capable of undergoing racemization through rapid allylic rearrangements. Furthermore, the B-(cycloalk-2-enyl)diisopinocampheylboranes achieve allylborations of aldehydes at -78-degrees-C and afford 1-(cycloalk-2-enyl)alkan-1-ols in 90-95% ee and 100% syn-diastereoselectivity.

引用

页码：2633 / 2638

页数：6

共 52 条

[1]

BARTLETT PA, 1980, TETRAHEDRON, V36, P3

[2]

BREWSTER JH, 1959, J AM CHEM SOC, V81, P5943

[3]

BROWN CA, 1966, J ORG CHEM, V31, P398

[4] B-2'-ISOPRENYLDIISOPINOCAMPHEYLBORANE - AN EFFICIENT REAGENT FOR THE CHIRAL ISOPRENYLATION OF ALDEHYDES - A CONVENIENT ROUTE TO BOTH ENANTIOMERS OF IPSENOL AND IPSDIENOL [J].

BROWN, HC ;

RANDAD, RS .

TETRAHEDRON LETTERS, 1990, 31 (04) :455-458

[5] CHIRAL SYNTHESIS VIA ORGANOBORANES .13. A HIGHLY DIASTEREOSELECTIVE AND ENANTIOSELECTIVE ADDITION OF [(Z)-GAMMA-ALKOXYALLYL]DIISOPINOCAMPHEYLBORANES TO ALDEHYDES [J].

BROWN, HC ;

JADHAV, PK ;

BHAT, KS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) :1535-1538

[6] ASYMMETRIC-SYNTHESIS OF THE DIASTEREOMERIC 1-(2-CYCLOHEXENYL)-1-ALKANOLS IN HIGH OPTICAL PURITY VIA A STEREOCHEMICALLY STABLE ALLYLIC BORANE, B-2-CYCLOHEXEN-1-YLDIISOPINOCAMPHEYLBORANE [J].

BROWN, HC ;

JADHAV, PK ;

BHAT, KS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (08) :2564-2565

[7] 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

[8] HYDROBORATION .76. HYDROBORATION OF CYCLIC DIENES WITH REPRESENTATIVE HYDROBORATING AGENTS [J].

BROWN, HC ;

BHAT, KS .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :445-449

[9] ENANTIOMERIC (Z)-CROTYLDIISOPINOCAMPHEYLBORANE AND (E)-CROTYLDIISOPINOCAMPHEYLBORANE - SYNTHESIS IN HIGH OPTICAL PURITY OF ALL 4 POSSIBLE STEREOISOMERS OF BETA-METHYLHOMOALLYL ALCOHOLS [J].

BROWN, HC ;

BHAT, KS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (02) :293-294

[10] 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

← 1 2 3 4 5 6 →