由2-亚磺酰基二烯合成无环1,4-二醇和1,4-氨基醇中的远程立体控制
Remote stereocontrol in the synthesis of acyclic 1,4-diols and 1,4-aminoalcohols from 2-sulfinyl dienes.
作者信息
Fernández de la Pradilla Roberto, Velado Marina, Colomer Ignacio, Simal Carmen, Viso Alma, Gornitzka Heinz, Hemmert Catherine
机构信息
Instituto de Química Orgánica General, IQOG-CSIC, Juan de la Cierva 3, 28006 Madrid, Spain.
出版信息
Org Lett. 2014 Oct 3;16(19):5200-3. doi: 10.1021/ol502592y. Epub 2014 Sep 24.
The highly diastereoselective conjugate addition of alcohols and amines (RXH) to enantiopure 2-sulfinyl dienes renders transient allylic sulfoxides which undergo sulfoxide-sulfenate rearrangement and sulfenate cleavage providing 2-ene-1,4-diols and 2-ene-1,4-aminoalcohols with up to 99:1 dr. The method allows for the generation of two stereocenters in a single synthetic operation with remote chirality transfer of one center into the other.
醇和胺（RXH）对对映体纯的2-亚磺酰基二烯进行的高度非对映选择性共轭加成生成了瞬态烯丙基亚砜，这些亚砜会发生亚砜-亚磺酸酯重排和亚磺酸酯裂解，从而提供高达99:1的非对映体比例的2-烯-1,4-二醇和2-烯-1,4-氨基醇。该方法允许在单一合成操作中生成两个立体中心，并将一个中心的远程手性转移到另一个中心。
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