Highly Enantioselective Alkynylation of α-Keto Ester: An Efficient Method for Constructing a Chiral Tertiary Carbon Center

作者: Biao Jiang , Zili Chen , Xiaoxia Tang

DOI: 10.1021/OL026544I

关键词:

摘要: The asymmetric addition of terminal alkynes to α-keto ester was carried out using a catalytic amount (1S,2S)-3-(tert-butyldimethylsilyloxyl)-2-N,N-(dimethylamino)-1-(p-nitrophenyl)-propane-1-ol in the presence Zn(OTf)2 give corresponding tertiary propargylic alcohols high yields with up 94% ee. N-Methylephedrine and Zn(OSO2CHF2)2 were also examined this reaction.

参考文章(15)
D. E. Frantz, R. Fässler, C. S. Tomooka, E. M. Carreira, The Discovery of Novel Reactivity in the Development of C−C Bond-Forming Reactions: In Situ Generation of Zinc Acetylides with ZnII/R3N Accounts of Chemical Research. ,vol. 33, pp. 373- 381 ,(2000) , 10.1021/AR990078O
So Won Youn, Yong Hae Kim, Jeong-Wook Hwang, Youngkyu Do, Highly diastereoselective additions of methoxyallene and acetylenes to chiral α-keto amides Chemical Communications. pp. 996- 997 ,(2001) , 10.1039/B100355K
Andrew G. Myers, Bin Zheng, New and Stereospecific Synthesis of Allenes in a Single Step from Propargylic Alcohols Journal of the American Chemical Society. ,vol. 118, pp. 4492- 4493 ,(1996) , 10.1021/JA960443W
Neel K. Anand, Erick M. Carreira, A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes. Journal of the American Chemical Society. ,vol. 123, pp. 9687- 9688 ,(2001) , 10.1021/JA016378U
Doug E. Frantz, Roger Fässler, Erick M. Carreira, Facile Enantioselective Synthesis of Propargylic Alcohols by Direct Addition of Terminal Alkynes to Aldehydes Journal of the American Chemical Society. ,vol. 122, pp. 1806- 1807 ,(2000) , 10.1021/JA993838Z
Ming Yi Chen, Jim Min Fang, An asymmetric synthesis of crobarbatic acid Journal of Organic Chemistry. ,vol. 57, pp. 2937- 2941 ,(1992) , 10.1021/JO00036A034
Lushi Tan, Cheng-yi Chen, Richard D. Tillyer, Edward J. J. Grabowski, Paul J. Reider, A Novel, Highly Enantioselective Ketone Alkynylation Reaction Mediated by Chiral Zinc Aminoalkoxides Angewandte Chemie International Edition. ,vol. 38, pp. 711- 713 ,(1999) , 10.1002/(SICI)1521-3773(19990301)38:5<711::AID-ANIE711>3.0.CO;2-W
Lin Pu, Hong-Bin Yu, Catalytic Asymmetric Organozinc Additions to Carbonyl Compounds Chemical Reviews. ,vol. 101, pp. 757- 824 ,(2001) , 10.1021/CR000411Y