Enantiomerically pure cyclobutane derivatives and their use in organic synthesis

被引:486
作者
Lee-Ruff, E [1 ]
Mladenova, G [1 ]
机构
[1] York Univ, Dept Chem, N York, ON M3J 1P3, Canada
关键词
D O I
10.1021/cr010013a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The importance of cyclobutanes as intermediates in organic synthesis has been recognized in the last 30 years. The availability of enantiomerically enriched derivatives for their use in chiral synthesis has spurred new methods for their preparation. Most of these developments occurred in the last 15 years. Effective methods include photochemical and catalyzed [2+2] cycloadditions with alkenes possessing chiral auxiliary groups which are either covalently or noncovalently bonded to the reacting partners. Many of these approaches are in their infancy and require further exploitation.
引用
收藏
页码:1449 / 1483
页数:35
相关论文
共 220 条
[91]   AN ENANTIOSELECTIVE SYNTHESIS OF 3,4-DISUBSTITUTED BUTYROLACTONES [J].
HONDA, T ;
KIMURA, N .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (01) :77-78
[92]   MODELS FOR ASYMMETRIC [2+2] CYCLO-ADDITIONS [J].
HOUGE, C ;
FRISQUEHESBAIN, AM ;
MOCKEL, A ;
GHOSEZ, L ;
DECLERCQ, JP ;
GERMAIN, G ;
VANMEERSSCHE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (10) :2920-2921
[93]   EFFICIENT SYNTHESES OF PROTECTED (2S,3S)-2,3-BIS(HYDROXYMETHYL)CYCLOBUTANONE, KEY INTERMEDIATES FOR THE SYNTHESIS OF CHIRAL CARBOCYCLIC ANALOGS OF OXETANOCIN [J].
HSIAO, CN ;
HANNICK, SM .
TETRAHEDRON LETTERS, 1990, 31 (46) :6609-6612
[94]   DILEMMA REGARDING AN ACTIVE-SITE MODEL FOR PORCINE PANCREATIC LIPASE [J].
HULTIN, PG ;
JONES, JB .
TETRAHEDRON LETTERS, 1992, 33 (11) :1399-1402
[95]   THE PHOTOCHEMISTRY OF VERBENONE [J].
HURST, JJ ;
WHITHAM, GH .
JOURNAL OF THE CHEMICAL SOCIETY, 1960, (JUL) :2864-2869
[96]   ENANTIO-SELECTIVE AND DIASTEREO-SELECTIVE SYNTHESIS OF CARBOCYCLIC OXETANOCIN ANALOGS [J].
ICHIKAWA, Y ;
NARITA, A ;
SHIOZAWA, A ;
HAYASHI, Y ;
NARASAKA, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (24) :1919-1921
[97]   ENANTIODIFFERENTIATING PHOTOCYCLODIMERIZATION OF PHENYL VINYL ETHERS AND 4-METHOXYSTYRENE SENSITIZED BY CHIRAL AROMATIC ESTERS [J].
INOUE, Y ;
OKANO, T ;
YAMASAKI, N ;
TAI, A .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1992, 66 (01) :61-68
[98]   ZIRCONIUM-MEDIATED, HIGHLY DIASTEREOSELECTIVE RING CONTRACTION OF CARBOHYDRATE-DERIVATIVES - SYNTHESIS OF HIGHLY FUNCTIONALIZED, ENANTIOMERICALLY PURE CARBOCYCLES [J].
ITO, H ;
MOTOKI, Y ;
TAGUCHI, T ;
HANZAWA, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (19) :8835-8836
[99]   ZIRCONIUM-MEDIATED RING CONTRACTION - AN EFFICIENT SYNTHESIS OF ENANTIOMERICALLY PURE KEY INTERMEDIATE OF CARBOCYCLIC OXETANOCIN [J].
ITO, H ;
TAGUCHI, T ;
HANZAWA, Y .
TETRAHEDRON LETTERS, 1993, 34 (47) :7639-7640
[100]  
Johnson R.A., 1991, Comprehensive Organic Synthesis, V7