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手性1,3 -二醇连续亲核和亲电烯丙基化反应中催化剂导向的非对映和位点选择性:取代吡喃的无保护基合成

Catalyst-directed diastereo- and site-selectivity in successive nucleophilic and electrophilic allylations of chiral 1,3-diols: protecting-group-free synthesis of substituted pyrans.

作者信息

Shin Inji, Wang Gang, Krische Michael J

机构信息

University of Texas at Austin, Department of Chemistry, 1 University Station - A5300, Austin, TX 78712-1167 (USA).

出版信息

Chemistry. 2014 Oct 6;20(41):13382-9. doi: 10.1002/chem.201404065. Epub 2014 Aug 28.

Abstract

The iridium-catalyzed, protecting group-free synthesis of 4-hydroxy-2,6-cis- or trans-pyrans through successive nucleophilic and electrophilic allylations of chiral 1,3-diols occurs with complete levels of catalyst-directed diastereoselectivity in the absence of protecting groups, premetallated reagents, or discrete alcohol-to-aldehyde redox reactions.

摘要

通过手性1,3 -二醇的连续亲核和亲电烯丙基化反应,铱催化的、无保护基的4 -羟基- 2,6 -顺式或反式吡喃的合成在没有保护基、预金属化试剂或离散的醇到醛氧化还原反应的情况下,以完全的催化剂导向非对映选择性水平发生。

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本文引用的文献

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4
Asymmetric catalysis at a distance: catalytic, site-selective phosphorylation of teicoplanin.
J Am Chem Soc. 2013 Aug 21;135(33):12414-21. doi: 10.1021/ja406067v. Epub 2013 Aug 7.
5
Regioselective silylation of pyranosides using a boronic acid/Lewis base co-catalyst system.
Org Biomol Chem. 2013 Sep 7;11(33):5409-12. doi: 10.1039/c3ob40981c.
6
Chemical tailoring of teicoplanin with site-selective reactions.
J Am Chem Soc. 2013 Jun 5;135(22):8415-22. doi: 10.1021/ja4038998. Epub 2013 May 21.
7
Synthesis of cardiac glycoside analogs by catalyst-controlled, regioselective glycosylation of digitoxin.
Org Lett. 2013 Mar 15;15(6):1358-61. doi: 10.1021/ol4003042. Epub 2013 Mar 6.
8
Formation of C-C bonds via ruthenium-catalyzed transfer hydrogenation().
Pure Appl Chem. 2012;84(8):1729-1739. doi: 10.1351/PAC-CON-11-10-18. Epub 2012 Mar 13.
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