期刊
TETRAHEDRON
卷 66, 期 25, 页码 4604-4620出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.04.027
关键词
Conjugate addition; Homochiral ammonia equivalent; Isoxazolidin-5-ones; beta(2,2,3)-Trisubstituted amino acids
Conjugate addition of the homochiral ammonia equivalent lithium N-tert-butyldimethylsilyloxy-N-(alpha-methylbenzyl)amide to a range of alpha,beta-unsaturated esters gives the corresponding beta-amino esters in moderate to good levels of diastereoselectivity. O-Desilylation and cyclisation furnishes homochiral soxazolidin-5-ones in >99:1 dr after purification. Sequential alkylation of these templates proceeds to give the corresponding 3,4-anti-disubstituted and 3,4,4-trisubstituted derivatives as single diastereoisomers after purification. The first alkylation occurs with high levels of diastereoselectivity on the face of the enolate anti to the C(3)-substituent, whereas the facial selectivity of the second alkylation is governed by a chiral relay effect, which depends upon the relative steric bulk of both the C(3)- and C(4)-substituents. Subsequent hydrogenolysis promotes cleavage of both the N-alpha-methylbenzyl group and the N-O bond within the isoxazolidin-5-one ring in one pot to give the corresponding beta(2,2,3)-tri-substituted amino acids directly. (C) 2010 Elsevier Ltd. All rights reserved.
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