Synthesis of enantiopure homoallylic alcohols and ethers by diastereoselective allylation of aldehydes

LF Tietze, K Schiemann, C Wegner…

文献索引：Tietze, Lutz F.; Schiemann, Kai; Wegner, Christoph; Wulff, Christian Chemistry--A European Journal, 1996 , vol. 2, # 9 p. 1164 - 1172

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被引用次数: 35

摘要

Abstract Enantiopure homoallylic alcohols 5, which are important building blocks in organic synthesis, are obtained with an ee of greater than 99% and a yield of 75–95% by cleavage of the secondary homoallylic ethers 4 using sodium in liquid ammonia. The ethers 4 are formed with excellent diastereoselectivity and in 52–89% yield by treatment of the aldehydes 1 with the trimethylsilyl ether of N-trifluoroacetylnorpseudoephedrine (2) in the presence of ...