ENANTIOSPECIFIC PREPARATION OF [(2R, 6S)-ENDO]-5-AZA-1,10,10-TRIMETHYL-3-OXATRICYCLO[5.2.1.0(2,6)]DECAN-4-ONE BY A NITRENE-MEDIATED ROUTE FROM [(1S)-ENDO]-(-)-BORNEOL AND ITS UTILITY AS A CHIRAL AUXILIARY IN SOME ASYMMETRIC TRANSFORMATIONS

被引:43
作者
BANKS, MR [1 ]
BLAKE, AJ [1 ]
CADOGAN, JIG [1 ]
DAWSON, IM [1 ]
GOSNEY, I [1 ]
GRANT, KJ [1 ]
GAUR, S [1 ]
HODGSON, PKG [1 ]
KNIGHT, KS [1 ]
SMITH, GW [1 ]
STEVENSON, DE [1 ]
机构
[1] BP INT LTD,SUNBURY RES CTR,SUNBURY TW16 7LN,MIDDX,ENGLAND
关键词
D O I
10.1016/S0040-4020(01)80472-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Attempted chiral aziridination of styrene by addition of optically-active alkoxycarbonylnitrene 5 derived from [(1s)-endo]-(-)-bornyl p-nitrobenzenesulphonoxycarbonate 4 is reported. No measurable asymmetric induction is observed under the various conditions employed, but in the absence of alkene, a tricyclic oxazolidin-2-one 8 is formed to which preparatively simpler access can be gained by thermal decomposition of azidoformate 7, either in 1,1,2,2-tetrachloroethane (50%) or by spray pyrolysis (58%). The oxazolidin-2-one 8 is demonstrated to be a successful chiral auxiliary by contemporary standards in a variety of asymmetric transformations, including alkylation, acylation, and aldol reactions for which high levels of asymmetric induction are observed. Diethylaluminium chloride-catalysed Diels-Alder reactions exhibit poorer selectivity except for the cinnamoyl derivative 23 which is stereospecific.
引用
收藏
页码:7979 / 8006
页数:28
相关论文
共 33 条
[1]  
AITKEN RA, 1984, TETRAHEDRON, V40, P2487
[2]  
[Anonymous], ASYMMETRIC SYNTHESIS
[3]  
ATKINSON RS, 1986, J CHEM SOC CHEM COMM, P832, DOI 10.1039/c39860000832
[4]   OXIDATION OF N-AMINOQUINAZOLONES IN THE PRESENCE OF ALKENES - EVIDENCE AGAINST INVOLVEMENT OF N-NITRENES [J].
ATKINSON, RS ;
KELLY, BJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (18) :1362-1363
[5]   ASYMMETRIC ALDOL REACTIONS - A NEW CAMPHOR-DERIVED CHIRAL AUXILIARY GIVING HIGHLY STEREOSELECTIVE ALDOL REACTIONS OF BOTH LITHIUM AND TITANIUM(IV) ENOLATES [J].
BONNER, MP ;
THORNTON, ER .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (04) :1299-1308
[6]   ENANTIOMERICALLY PURE DIHYDROPYRIMIDINONES AS REAGENTS AND AUXILIARIES FOR ASYMMETRIC-SYNTHESIS [J].
CHU, KS ;
NEGRETE, GR ;
KONOPELSKI, JP ;
LAKNER, FJ ;
WOO, NT ;
OLMSTEAD, MM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1800-1812
[7]  
CLANCY M, 1982, J CHEM RES-S, P78
[8]   THE PREPARATION OF OPTICALLY-ACTIVE DELTA-2-ISOXAZOLINES - A MODEL FOR ASYMMETRIC INDUCTION IN THE NON LEWIS ACID-CATALYZED REACTIONS OF OPPOLZERS CHIRAL SULTAM [J].
CURRAN, DP ;
KIM, BH ;
DAUGHERTY, J ;
HEFFNER, TA .
TETRAHEDRON LETTERS, 1988, 29 (29) :3555-3558
[9]   ASYMMETRIC DIELS-ALDER CYCLO-ADDITION REACTIONS WITH CHIRAL ALPHA, BETA-UNSATURATED N-ACYLOXAZOLIDINONES [J].
EVANS, DA ;
CHAPMAN, KT ;
BISAHA, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) :1238-1256
[10]   STEREOSELECTIVE ALDOL CONDENSATIONS VIA BORON ENOLATES [J].
EVANS, DA ;
NELSON, JV ;
VOGEL, E ;
TABER, TR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) :3099-3111