Iterative Cr-mediated catalytic asymmetric allylation to synthesize syn/syn- and anti/anti-1,3,5-triols.

Iterative Cr-mediated catalytic asymmetric allylation to synthesize syn/syn- and anti/anti-1,3,5-triols.
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DOI:
10.1021/ol801094e
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发表时间:
2008-06
期刊:
影响因子:
5.2
通讯作者:
Zhiyu Zhang;Sylvain Aubry;Y. Kishi
Zhiyu Zhang;Sylvain Aubry;Y. Kishi
中科院分区:
化学1区
文献类型:
--
作者:
Zhiyu Zhang;Sylvain Aubry;Y. Kishi

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重复使用铬介导的催化不对称烯丙化反应可以简单地获得1,3-多元醇。以SYN/SYN-和抗/抗1,3,5-三醇为代表,研究了该方法的可行性,从而证明了(1)预先存在的TMS保护的β-位醇对铬催化的不对称烯丙化反应没有显著影响;(2)该合成路线在不对称诱导和产率的有用水平上提供了预期的SYN/SYN-和抗/抗1,3,5-三醇。
Iterative use of Cr-mediated catalytic asymmetric allylation could give a simple access to 1,3-polyols. Using syn/syn- and anti/anti-1,3,5-triols as representative examples, the feasibility of this approach is studied, thereby demonstrating that (1) the pre-existing TMS-protected alcohol at the beta-position does not give a significant effect on the Cr-mediated catalytic asymmetric allylation and (2) this synthetic route furnishes the expected syn/syn- and anti/anti-1,3,5-triols at the useful level of asymmetric induction and yield.