Catalytic Enantioselective Assembly of Homoallylic Alcohols from Dienes, Aryldiazonium Salts, and Aldehydes

Zhong-Lin Tao; Alafate Adili; Hong-Cheng Shen; Zhi-Yong Han; Liu-Zhu Gong

doi:10.1002/anie.201600148

Catalytic Enantioselective Assembly of Homoallylic Alcohols from Dienes, Aryldiazonium Salts, and Aldehydes

Angew Chem Int Ed Engl. 2016 Mar 18;55(13):4322-6. doi: 10.1002/anie.201600148. Epub 2016 Feb 25.

Authors

Zhong-Lin Tao¹, Alafate Adili¹, Hong-Cheng Shen¹, Zhi-Yong Han¹, Liu-Zhu Gong^{2

3

4}

Affiliations

¹ Hefei National Laboratory for Physical Sciences at Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China.
² Hefei National Laboratory for Physical Sciences at Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China. gonglz@ustc.edu.cn.
³ Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, China. gonglz@ustc.edu.cn.
⁴ High Magnetic Field Laboratory, Hefei Institutes of Physical Science, CAS, Hefei, 230031, China. gonglz@ustc.edu.cn.

PMID: 26919187
DOI: 10.1002/anie.201600148

Abstract

A highly selective multicomponent carbonyl allylation reaction of 1,3-butadienes, aryldiazonium tetrafluoroborates, and aldehydes has been established under the combined catalysis of palladium acetate and chiral anion phase transfer to render the favorable assembly of chiral Z-configured homoallylic alcohols in high yields and with excellent levels of enantioselectivity.

Keywords: allylic compounds; asymmetric catalysis; multicomponent reactions; palladium; phase-transfer catalysis.

Publication types

Research Support, Non-U.S. Gov't