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通过炔基硅烷催化加成到α-硅氧基醛上高非对映选择性地制备反式-1,2-二醇

Highly diastereoselective preparation of anti-1,2-diols by catalytic addition of alkynylsilanes to alpha-silyloxyaldehydes.

作者信息

Sa-ei Kanicha, Montgomery John

机构信息

Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.

出版信息

Org Lett. 2006 Sep 28;8(20):4441-3. doi: 10.1021/ol061579u.

DOI:10.1021/ol061579u
PMID:16986920
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2720632/
Abstract

The catalytic, diastereoselective coupling of alpha-silyloxy aldehydes and alkynylsilanes catalyzed by a nickel(0) N-heterocyclic carbene complex provides an effective entry to anti-1,2-diols. The scope of couplings and extent of diastereoselection are excellent across a range of substrates.

摘要

镍(0)氮杂环卡宾配合物催化的α-硅氧基醛与炔基硅烷的催化非对映选择性偶联反应为制备反式-1,2-二醇提供了一条有效途径。在一系列底物中,偶联反应的范围和非对映选择性程度都非常出色。

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Org Lett. 2006 Mar 16;8(6):1181-4. doi: 10.1021/ol0600786.
2
Access to macrocyclic endocyclic and exocyclic allylic alcohols by nickel-catalyzed reductive cyclization of ynals.通过镍催化的烯醛还原环化反应合成大环内烯丙醇和外烯丙醇
J Am Chem Soc. 2005 Sep 28;127(38):13156-7. doi: 10.1021/ja054590i.
3
anti-1,2-Diols via Ni-catalyzed reductive coupling of alkynes and alpha-oxyaldehydes.通过镍催化炔烃与α-氧代醛的还原偶联反应制备反式-1,2-二醇
Org Lett. 2005 Jul 7;7(14):2937-40. doi: 10.1021/ol050881k.
4
A pentenyl dianion-based strategy for convergent synthesis of ene-1,5-diols.一种基于戊烯基双负离子的烯-1,5-二醇汇聚合成策略。
J Am Chem Soc. 2005 Mar 23;127(11):3694-5. doi: 10.1021/ja050039+.
5
Ligand-switchable directing effects of tethered alkenes in nickel-catalyzed additions to alkynes.镍催化炔烃加成反应中 tethered 烯烃的配体可切换导向效应
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6
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Science. 2004 Sep 17;305(5691):1752-5. doi: 10.1126/science.1101710. Epub 2004 Aug 12.
7
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