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 ...
