Radical-based asymmetric synthesis: an iterative approach to 1, 3, 5, ... (2n + 1) polyols.
Radical-based asymmetric synthesis: an iterative approach to 1, 3, 5, ... (2n + 1) polyols.
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基于自由基的不对称合成：1, 3, 5, ... (2n 1) 多元醇的迭代方法。
DOI：
10.1021/ol990188v
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发表时间：
1999
期刊：
影响因子：
5.2
通讯作者：
Anderson,JT
中科院分区：
文献类型：
--
作者：
Garner,P;Anderson,JT
一种概念上新颖的方法，以1，3，5，. (2n+ 1）多元醇的合成方法。从α-酮酯前体开始，一般顺序为（1）酮还原，（2）辅助连接，（3）皂化，（4）巴顿酯化，（5）自由基加成，以70 - 80%的总产率得到两碳同系物。这种迭代策略的简单性和通用性为1，3，5，…(2n+ 1）多元醇合成提出了制备含有该结构基序的分子的有吸引力的替代方案。
A conceptually novel approach to 1, 3, 5, ... (2n+ 1) polyols based on iterative stereocontrolled homologation of chiral hydroxyalkyl radicals is reported. Starting from α-keto ester precursors, the general sequence of (1) ketone reduction, (2) auxiliary attachment, (3) saponification, (4) Barton esterification, and (5) radical addition provided the two-carbon homologue in 70−80% overall yield. The simplicity and generality of this iterative strategy for 1, 3, 5, ... (2n+ 1) polyol synthesis suggests an attractive alternative for the preparation of molecules containing this structural motif.