1,7-asymmetric induction in a nitrogen ring expansion process facilitated by in situ tethering

被引:27
作者
Furness, K [1 ]
Aubé, J [1 ]
机构
[1] Univ Kansas, Dept Med Chem, Lawrence, KS 66045 USA
关键词
D O I
10.1021/ol990685b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] There are only a few methods for the asymmetric ring expansion of prochiral ketones. Symmetrically substituted cyclohexanones can be converted to the corresponding ring expanded caprolactam with excellent 1,7 diastereoselectivity (greater than or equal to 93% ds) and yields (greater than or equal to 86%), using a chiral hydroxy azide-mediated Schmidt reaction.
引用
收藏
页码:495 / 497
页数:3
相关论文
共 40 条
[1]   APPLICATION OF ENZYMATIC BAEYER-VILLIGER OXIDATIONS OF 2-SUBSTITUTED CYCLOALKANONES TO THE TOTAL SYNTHESIS OF (R)-(+)-LIPOIC ACID [J].
ADGER, B ;
BES, MT ;
GROGAN, G ;
MCCAGUE, R ;
PEDRAGOSAMOREAU, S ;
ROBERTS, SM ;
VILLA, R ;
WAN, PWH ;
WILLETTS, AJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (15) :1563-1564
[2]   MICROBIAL TRANSFORMATIONS .16. ONE-STEP SYNTHESIS OF A PIVOTAL PROSTAGLANDIN CHIRAL SYNTHON VIA A HIGHLY ENANTIOSELECTIVE MICROBIOLOGICAL BAEYER-VILLIGER TYPE REACTION [J].
ALPHAND, V ;
ARCHELAS, A ;
FURSTOSS, R .
TETRAHEDRON LETTERS, 1989, 30 (28) :3663-3664
[3]  
ALPHAND V, 1990, J ORG CHEM, V55, P437
[4]   SELECTIVITY IN AN ASYMMETRIC NITROGEN INSERTION PROCESS [J].
AUBE, J ;
BURGETT, PM ;
WANG, Y .
TETRAHEDRON LETTERS, 1988, 29 (02) :151-154
[5]   OXAZIRIDINE-MEDIATED RING EXPANSIONS OF SUBSTITUTED CYCLOBUTANONES - SYNTHESIS OF (-)-GAMMA-AMINO-BETA-HYDROXYBUTYRIC ACID (GABOB) [J].
AUBE, J ;
WANG, YG ;
GHOSH, S ;
LANGHANS, KL .
SYNTHETIC COMMUNICATIONS, 1991, 21 (05) :693-701
[6]   Oxaziridine rearrangements in asymmetric synthesis [J].
Aube, J .
CHEMICAL SOCIETY REVIEWS, 1997, 26 (04) :269-277
[7]   SYNTHESES AND REARRANGEMENTS OF SPIROCYCLIC OXAZIRIDINES DERIVED FROM UNSYMMETRICAL KETONES [J].
AUBE, J ;
HAMMOND, M ;
GHERARDINI, E ;
TAKUSAGAWA, F .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :499-508
[8]   CORRECTION [J].
AUBE, J .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :4086-4086
[9]   TICL4-MEDIATED REACTIONS OF ALKYL AZIDES WITH CYCLIC-KETONES [J].
AUBE, J ;
MILLIGAN, GL ;
MOSSMAN, CJ .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1635-1637
[10]   SYNTHETIC ASPECTS OF AN ASYMMETRIC NITROGEN-INSERTION PROCESS - PREPARATION OF CHIRAL, NON-RACEMIC CAPROLACTAMS AND VALEROLACTAMS - TOTAL SYNTHESIS OF (-)-ALLOYOHIMBANE [J].
AUBE, J ;
WANG, YG ;
HAMMOND, M ;
TANOL, M ;
TAKUSAGAWA, F ;
VANDERVELDE, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) :4879-4891