Remote Stereocontrolled Construction of Vicinal Axially Chiral Tetrasubstituted Allenes and Heteroatom-Functionalized Quaternary Carbon Stereocenters

Pei Zhang; Qiuhong Huang; Yuyu Cheng; Rongshi Li; Pengfei Li; Wenjun Li

doi:10.1021/acs.orglett.8b03801

Remote Stereocontrolled Construction of Vicinal Axially Chiral Tetrasubstituted Allenes and Heteroatom-Functionalized Quaternary Carbon Stereocenters

Pei Zhang, Qiuhong Huang, Yuyu Cheng, Rongshi Li, Pengfei Li, Wenjun Li

Research output: Contribution to journal › Article › peer-review

63 Scopus citations

Abstract

The direct diastereo- and enantioselective 1,8-conjugate additions of thiazolones and azlactones, respectively, to para-quinone methides generated in situ from propargylic alcohols have been achieved in the presence of chiral phosphoric acids. The remote stereocontrolled activation protocol provides an efficient and facile approach for the construction of vicinal axially chiral tetrasubstituted allenes and heteroatom-functionalized quaternary carbon stereocenters, which expands the synthetic potential of chiral phosphoric acids.

Original language	English (US)
Pages (from-to)	503-507
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	2
DOIs	https://doi.org/10.1021/acs.orglett.8b03801
State	Published - Jan 18 2019
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "The direct diastereo- and enantioselective 1,8-conjugate additions of thiazolones and azlactones, respectively, to para-quinone methides generated in situ from propargylic alcohols have been achieved in the presence of chiral phosphoric acids. The remote stereocontrolled activation protocol provides an efficient and facile approach for the construction of vicinal axially chiral tetrasubstituted allenes and heteroatom-functionalized quaternary carbon stereocenters, which expands the synthetic potential of chiral phosphoric acids.",

author = "Pei Zhang and Qiuhong Huang and Yuyu Cheng and Rongshi Li and Pengfei Li and Wenjun Li",

note = "Funding Information: The authors acknowledge the financial support from National Natural Science Foundation of China (21502043, 21871128), the Natural Science Foundation of Shandong Province (ZR2017JL011), and the Shenzhen Nobel Prize Scientists Laboratory Project (C17783101). Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

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AU - Zhang, Pei

AU - Huang, Qiuhong

AU - Cheng, Yuyu

AU - Li, Rongshi

AU - Li, Pengfei

AU - Li, Wenjun

N1 - Funding Information: The authors acknowledge the financial support from National Natural Science Foundation of China (21502043, 21871128), the Natural Science Foundation of Shandong Province (ZR2017JL011), and the Shenzhen Nobel Prize Scientists Laboratory Project (C17783101). Publisher Copyright: © 2019 American Chemical Society.

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N2 - The direct diastereo- and enantioselective 1,8-conjugate additions of thiazolones and azlactones, respectively, to para-quinone methides generated in situ from propargylic alcohols have been achieved in the presence of chiral phosphoric acids. The remote stereocontrolled activation protocol provides an efficient and facile approach for the construction of vicinal axially chiral tetrasubstituted allenes and heteroatom-functionalized quaternary carbon stereocenters, which expands the synthetic potential of chiral phosphoric acids.

AB - The direct diastereo- and enantioselective 1,8-conjugate additions of thiazolones and azlactones, respectively, to para-quinone methides generated in situ from propargylic alcohols have been achieved in the presence of chiral phosphoric acids. The remote stereocontrolled activation protocol provides an efficient and facile approach for the construction of vicinal axially chiral tetrasubstituted allenes and heteroatom-functionalized quaternary carbon stereocenters, which expands the synthetic potential of chiral phosphoric acids.

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Remote Stereocontrolled Construction of Vicinal Axially Chiral Tetrasubstituted Allenes and Heteroatom-Functionalized Quaternary Carbon Stereocenters

Abstract

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