THE USE OF B-[(E)-3-(DIPHENYLAMINO)ALLYL[DIISOPINOCAMPHEYLBORANE AS A REAGENT FOR THE STEREOSELECTIVE SYNTHESIS OF ANTI-BETA-DIPHENYLAMINO ALCOHOLS AND TRANS-1-DIPHENYLAMINO-2-(1-HYDROXYALKYL) CYCLOROPANES

被引:35
作者
BARRETT, AGM [1 ]
SEEFELD, MA [1 ]
机构
[1] COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80523
关键词
D O I
10.1016/S0040-4020(01)88011-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
anti-beta-Amino alcohols and trans-1-amino-2-(1-hydroxyalkyl) cyclopropanes have been produced with high relative and absolute stereocontrol in a simple one-pot process via the reaction of aldehydes with B-[(E)-3-(diphenylamino)allyl]-diisopinocampheylborane and a subsequent alkaline hydrogen peroxide work-up.
引用
收藏
页码:7857 / 7870
页数:14
相关论文
共 22 条
[1]  
ANDERSON OP, UNPUB
[2]   B-[(E)-3-(DIPHENYLAMINO)ALLYL]DIISOPINOCAMPHEYLBORANE - AN EXCELLENT REAGENT FOR THE STEREOSELECTIVE SYNTHESIS OF ANTI-BETA-DIPHENYLAMINO ALCOHOLS [J].
BARRETT, AGM ;
SEEFELD, MA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (04) :339-341
[3]   B-[3-((DIISOPROPYLAMINO)DIMETHYLSILYL)ALLYL]DIISOPINOCAMPHEYLBORANE - AN EXCELLENT REAGENT FOR THE STEREOSELECTIVE SYNTHESIS OF ANTI VICINAL DIOLS [J].
BARRETT, AGM ;
MALECHA, JW .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) :5243-5245
[4]   DICHLOROISOPROPOXYTITANIUM NITRONATES AS REAGENTS FOR STEREOSELECTIVE HENRY REACTIONS [J].
BARRETT, AGM ;
ROBYR, C ;
SPILLING, CD .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (06) :1233-1234
[5]   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
[7]  
Bycroft B. W., 1988, DICT ANTIBIOTICS REL
[8]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[9]   FUNCTIONALIZED ORGANOLITHIUM REAGENTS .9. LITHIATION AND ISOMERIZATION OF ALLYLIC AMINES AS A GENERAL-ROUTE TO ENAMINES AND THEIR CARBONYL DERIVATIVES [J].
EISCH, JJ ;
SHAH, JH .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) :2955-2957
[10]   L-2-NITRO-1,3-ALKANEDIOLS BY STEREOSELECTIVE ADDITION OF NITROETHANOL TO ALDEHYDES - ON THE ASYMMETRIC ELECTROPHILIC ADDITION TO DOUBLE-BONDS [J].
EYER, M ;
SEEBACH, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (12) :3601-3606