Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 357, Issue 4, Pages 818-822Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201400992
Keywords
allylic compounds; amino acids; fluorine; ketimines; tetrasubstituted carbon stereocenters
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Funding
- National Natural Science Foundation of China [21102093, 21172148, 21472126]
- Science and Technology Commission of Shanghai Municipality [12XD1404600]
- Innovation Program of Shanghai Municipal Education Commission [14YZ144]
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Highly regio-and diastereoselective 1,2-addition of organolithium reagents to chiral fluoroalkyl alpha,beta-unsaturated N-tert-butanesulfinyl ketimines was developed, providing a general and efficient method for the asymmetric synthesis of structurally diverse alpha-tertiary fluoroalkyl allylic amines in high yields and with excellent diastereoselectivities (dr up to >99: 1). The synthetic application of the method was demonstrated by the rapid and convenient preparation of challenging alpha-fluoroalkyl alpha-amino acids with alpha-tetrasubstituted carbon.
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