Selectively deuterated and optically active cyclic ethers

Y Kawakami, T Asai, K Umeyama…

Index: Kawakami, Yuhsuke; Asai, Tamio; Umeyama, Kiyoshi; Yamashita, Yuya Journal of Organic Chemistry, 1982 , vol. 47, # 18 p. 3581 - 3585

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Citation Number: 27

Abstract

The oxidation of 2 to potassium glycerate 2, 3-acetonide (3) is smooth; however, incomplete oxidation gives 3-methoxy-1, 2-propanediol acetonide as a side product, along with the main product 4, after treatment with CH31. The reduction of 4 by LAD afforded the selectively deuterated alcohol 5 in a reasonable yield. Baldwin synthesized (S)-18b from (S)-2 by the reaction path corresponding to path A in Scheme I. 6 The yield in the chlorination of 3-( ...