Comparative enantiocontrol with allyl phenyldiazoacetates in asymmetric catalytic intramolecular cyclopropanation

被引:13
作者
Doyle, MP [1 ]
Hu, WH [1 ]
Weathers, TM [1 ]
机构
[1] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
关键词
chiral dirhodium(II) carboxamidates; metal carbene reactions; azetidinone ligands; steric control;
D O I
10.1002/chir.10219
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Dirhodium(II) azetidinone-carboxylates are effective asymmetric catalysts for diazo, decomposition of allyl diazoacetates and their subsequent intramolecular cyclopropanations. The effect of alkene substituents on enantiocontrol has been examined and modest selectivities have been achieved. Steric influences from substituents on the diazo carbon are seen to diminish enantioselectivities.
引用
收藏
页码:369 / 373
页数:5
相关论文
共 16 条
[1]   DIAZOTRANSFER REACTIONS WITH PARA-ACETAMIDOBENZENESULFONYL AZIDE [J].
BAUM, JS ;
SHOOK, DA ;
DAVIES, HML ;
SMITH, HD .
SYNTHETIC COMMUNICATIONS, 1987, 17 (14) :1709-1716
[2]  
Davies H. M. L., 2001, ORG REACTIONS, V57, P1
[3]   Effect of diazoalkane structure on the stereoselectivity of rhodium(II) (S)-N-(arylsulfonyl)prolinate catalyzed cyclopropanations [J].
Davies, HML ;
Bruzinski, PR ;
Fall, MJ .
TETRAHEDRON LETTERS, 1996, 37 (24) :4133-4136
[4]  
Doyle M. P., 1998, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides
[5]   Recent advances in asymmetric catalytic metal carbene transformations [J].
Doyle, MP ;
Forbes, DC .
CHEMICAL REVIEWS, 1998, 98 (02) :911-935
[6]   Comparative evaluation of enantiocontrol for intramolecular cyclopropanation of diazoacetates with chiral Cu-I, Rh-II and Ru-II catalysts [J].
Doyle, MP ;
Peterson, CS ;
Zhou, QL ;
Nishiyama, H .
CHEMICAL COMMUNICATIONS, 1997, (02) :211-212
[7]   Dirhodium(II) tetrakis[methyl 2-oxaazetidine-4-carboxylate]: A chiral dirhodium(II) carboxamidate of exceptional reactivity and selectivity [J].
Doyle, MP ;
Davies, SB ;
Hu, WH .
ORGANIC LETTERS, 2000, 2 (08) :1145-1147
[8]  
Doyle MP, 2001, ADV SYNTH CATAL, V343, P299, DOI 10.1002/1615-4169(20010330)343:3<299::AID-ADSC299>3.0.CO
[9]  
2-Y
[10]  
Doyle MP, 1996, SYNLETT, P697