Tetrahedron

Use of the Claisen/metathesis reaction sequence for the synthesis of enantiomerically pure 1-aminocycloalkene-1-carboxylic acids

K Plé, A Haudrechy, NP Probst

文献索引：Ple, Karen; Haudrechy, Arnaud; Probst, Nicolas P. Tetrahedron, 2010 , vol. 66, # 27-28 p. 5030 - 5035

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被引用次数: 5

摘要

An effective method for the preparation of enantiomerically pure 1-aminocycloalkene-1- carboxylic acids is reported using a chelate Claisen rearrangement–metathesis sequence. Enantioselectivity is achieved through substrate control and a highly ordered transition state, without the use of a chiral auxiliary. A synthesis of 1-aminocyclopent-3-ene-1-carboxylic acid 1 in five steps and 47% overall yield is also described.