Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 30, Pages 11757-11765Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja2043563
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Funding
- National Natural Science Foundation of China [20972117]
- SRFDP [20090141110042]
- 973 Program [2011CB808600]
- Ministry of Education [IRT1030]
- Program for New Century Excellent Talents in University [NCET-10-0649]
- Fundamental Research Funds for the Central Universities
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A novel catalytic asymmetric Michael addition of azomethine ylide with beta-substituted alkylidene bisphosphates was realized in the presence of a chiral copper(I)/TF-BiphamPhos complex. The present system provides a unique and facile access to enantioenriched unnatural a-amino acid derivatives containing gem-bisphosphonates (gem-BPs) in high yields with excellent diastereoselectivities and enantioselectivities. Subsequent transformations lead to the expedient preparation of biologically active unnatural a-amino acid derivatives containing BPs and bisphosphonic acids without loss of diastereo- and enantiomeric excess.
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