STEREOCONTROLLED CYCLOPROPANATION OF ALPHA,BETA-UNSATURATED CARBOXAMIDES DERIVED FROM BICYCLIC AMINO-ALCOHOLS

被引：17
作者：
TANAKA, K
UNO, H
OSUGA, H
SUZUKI, H
机构：
[1] Department of Chemistry, Faculty of Science, Kyoto University, Sakyo, Kyoto
来源：
TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 07期
关键词：
D O I：
10.1016/0957-4166(94)80150-9
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The asymmetric cyclopropanation of the exo-N-[(1R,2S,3R,4S)-2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]hept-3-yl]-3-phenyl-2-propenamide and the endo-( 1R,2R,3S,4S)-isomer with Et(2)Zn/CH2I2 proceeded with predictable absolute stereochemistry. The exo-amide gave the (1R,2R)-cyclopropane derivative selectively (de less than or equal to 80%), while the endo-amide gave the (1S,2S)-isomer (de less than or equal to 58%). Complete reversal of the stereoselectivity (98% de) was observed when O-triisopropyl derivatives of the amides were used in the cyclopropanation.
引用
收藏
页码：1175 / 1178
页数：4
相关论文
共 52 条
[1]  
ABDALLAH H, 1982, TETRAHEDRON LETT, V23, P503
[2]   THE ASYMMETRIC-SYNTHESIS OF CIS-SUBSTITUTED CYCLOPROPANECARBOXYLIC ACID-DERIVATIVES [J].
AMBLER, PW ;
DAVIES, SG .
TETRAHEDRON LETTERS, 1988, 29 (52) :6979-6982
[3]   AN ASYMMETRIC SIMMONS-SMITH REACTION [J].
ARAI, I ;
MORI, A ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (26) :8254-8256
[4]   ASYMMETRIC-SYNTHESIS OF PERMETHRIC ACID - STEREOCHEMISTRY OF CHIRAL COPPER CARBENOID REACTION [J].
ARATANI, T ;
YONEYOSHI, Y ;
NAGASE, T .
TETRAHEDRON LETTERS, 1982, 23 (06) :685-688
[5]   ASYMMETRIC TOTAL SYNTHESIS OF THE INDIVIDUAL DIASTEREOISOMERS OF HYPOGLYCIN-A [J].
BALDWIN, JE ;
ADLINGTON, RM ;
BEBBINGTON, D ;
RUSSELL, AT .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (17) :1249-1251
[6]   ALLYLIC STEREOCENTER DIRECTED CYCLOPROPANATION - A NEW HIGHLY ENANTIOSELECTIVE SYNTHESIS OF HEMICARONIC ALDEHYDE [J].
BERNARDI, A ;
SCOLASTICO, C ;
VILLA, R .
TETRAHEDRON LETTERS, 1989, 30 (28) :3733-3734
[7]   ENANTIOSELECTIVE CYCLOPROPANE SYNTHESIS USING THE CHIRAL CARBENE COMPLEXES (SFESC)-(RFESC)-(C5H5)(CO)(PH2(S)-2-METHYBUTYLP)FE=CHCH3+ AND -(C5H5)(CO)(PH2(S)-2-METHYLBUTYLP)FE=CHCH3+ - ROLE OF METAL VS LIGAND CHIRALITY IN THE OPTICAL INDUCTION [J].
BROOKHART, M ;
TIMMERS, D ;
TUCKER, JR ;
WILLIAMS, GD ;
HUSK, GR ;
BRUNNER, H ;
HAMMER, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (22) :6721-6723
[8]   THE USE OF 1,2-TRANS-CYCLOHEXANEDIOL AS AN EFFICIENT CHIRAL AUXILIARY FOR THE ASYMMETRIC CYCLOPROPANATION OF ALLYLIC ETHERS [J].
CHARETTE, AB ;
MARCOUX, JF .
TETRAHEDRON LETTERS, 1993, 34 (45) :7157-7160
[9]   CARBOHYDRATES AS CHIRAL AUXILIARIES - ASYMMETRIC CYCLOPROPANATION REACTION OF ACYCLIC OLEFINS [J].
CHARETTE, AB ;
COTE, B ;
MARCOUX, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (21) :8166-8167
[10]   SYNTHESIS OF (+) DICTYOPTERENE A CONSTITUENT OF MARINE BROWN-ALGAE AND (+) DICTYOPTERENE C' BY CHIRALITY TRANSFER OF OPTICALLY-ACTIVE ALLYLIC BENZOATE WITH PALLADIUM (O) CATALYST [J].
COLOBERT, F ;
GENET, JP .
TETRAHEDRON LETTERS, 1985, 26 (23) :2779-2782
123456