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双功能二肽膦催化α-取代的丙二烯酸酯与β,γ-不饱和N-磺酰亚胺的对映选择性[3+2]环化反应

Enantioselective [3 + 2] annulation of α-substituted allenoates with β,γ-unsaturated N-sulfonylimines catalyzed by a bifunctional dipeptide phosphine.

作者信息

Ni Huanzhen, Yao Weijun, Lu Yixin

机构信息

Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543.

出版信息

Beilstein J Org Chem. 2016 Feb 24;12:343-8. doi: 10.3762/bjoc.12.37. eCollection 2016.

DOI:10.3762/bjoc.12.37
PMID:26977194
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4778533/
Abstract

The first enantioselective [3 + 2] annulation of α-substituted allenoates with β,γ-unsaturated N-sulfonylimines is described. In the presence of a dipeptide phosphine catalyst, a wide range of highly functionalized cyclopentenes bearing an all-carbon quaternary center were obtained in moderate to good yields and with good to excellent enantioselectivities.

摘要

本文描述了α-取代的丙二烯酸酯与β,γ-不饱和N-磺酰亚胺的首例对映选择性[3 + 2]环化反应。在二肽膦催化剂的存在下，可中等至良好的产率以及良好至优异的对映选择性得到一系列带有全碳季碳中心的高度官能化环戊烯。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/45f8/4778533/bd7267cf547f/Beilstein_J_Org_Chem-12-343-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/45f8/4778533/19935c603178/Beilstein_J_Org_Chem-12-343-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/45f8/4778533/bd7267cf547f/Beilstein_J_Org_Chem-12-343-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/45f8/4778533/19935c603178/Beilstein_J_Org_Chem-12-343-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/45f8/4778533/bd7267cf547f/Beilstein_J_Org_Chem-12-343-g003.jpg

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Chem Sci. 2015 Dec 1;6(12):7319-7325. doi: 10.1039/c5sc03135d. Epub 2015 Sep 15.
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Highly enantioselective construction of tertiary thioethers and alcohols phosphine-catalyzed asymmetric γ-addition reactions of 5-thiazol-4-ones and 5-oxazol-4-ones: scope and mechanistic understandings.叔硫醚和醇的高对映选择性构建：5-噻唑-4-酮和5-恶唑-4-酮的膦催化不对称γ-加成反应——范围与机理认识
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