Tetrahedron

Asymmetric synthesis of (R)-(+)-and (S)-(-)-2, 2, 4-trimethyl-4-(hydroxymethyl)-1, 3-dioxolane of high enantiomeric purity

D Tanner, P Somfai

文献索引：Tanner, David; Somfai, Peter Tetrahedron, 1986 , vol. 42, # 21 p. 5985 - 5990

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被引用次数: 27

摘要

The title compounds, 1 and 1', are readily available in four steps from 2-benzyloxymethyl-2- propen-1-ol, the key step being Sharpless asymmetric epoxidation to give the chiral epoxides 5 or 5'. The total chemical yield of 1 or 1'is 50%, the final products being obtained essentially optically pure. By suitable protecting group manipulation, both title enantiomers can be produced from either of the antipodal epoxides 5 or 5'.