Rhodium-Catalyzed Enantioselective Hydroselenation of Heterobicyclic Alkenes

Sifeng Li; Qingjing Yang; Zhaoxiang Bian; Jun Wang

doi:10.1021/acs.orglett.0c00762

Rhodium-Catalyzed Enantioselective Hydroselenation of Heterobicyclic Alkenes

Sifeng Li, Qingjing Yang, Zhaoxiang Bian^*, Jun Wang^*

^*Corresponding author for this work

School of Chinese Medicine

Research output: Contribution to journal › Journal article › peer-review

17 Citations (Scopus)

Abstract

A highly efficient Rh(I)/(S)-xyl-Binap catalytic system is developed for the asymmetric hydroselenation of various nonpolar olefins with diselenides. Under these mild reaction conditions, a wide range of heterobicyclic alkenes give selenol-incorporated adducts in excellent enantioselectivities (up to 97%) along with high yields (up to 96%) by overcoming self-promoted racemic hydroselenation. The strategy is also applied for kinetic resolution of unsymmetric oxabenzonorbornadiene.

Original language	English
Pages (from-to)	2781-2785
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	7
Early online date	20 Mar 2020
DOIs	https://doi.org/10.1021/acs.orglett.0c00762
Publication status	Published - 3 Apr 2020

Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Rhodium-Catalyzed Enantioselective Hydroselenation of Heterobicyclic Alkenes",

abstract = "A highly efficient Rh(I)/(S)-xyl-Binap catalytic system is developed for the asymmetric hydroselenation of various nonpolar olefins with diselenides. Under these mild reaction conditions, a wide range of heterobicyclic alkenes give selenol-incorporated adducts in excellent enantioselectivities (up to 97%) along with high yields (up to 96%) by overcoming self-promoted racemic hydroselenation. The strategy is also applied for kinetic resolution of unsymmetric oxabenzonorbornadiene.",

author = "Sifeng Li and Qingjing Yang and Zhaoxiang Bian and Jun Wang",

note = "Funding Information: We gratefully acknowledge financial support from the National Natural Science Foundation of China (NSFC 21971102) and Shenzhen Basic Research Program (JCYJ20170817112532779). Publisher copyright: {\textcopyright} 2020 American Chemical Society",

year = "2020",

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doi = "10.1021/acs.orglett.0c00762",

language = "English",

volume = "22",

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journal = "Organic Letters",

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TY - JOUR

T1 - Rhodium-Catalyzed Enantioselective Hydroselenation of Heterobicyclic Alkenes

AU - Li, Sifeng

AU - Yang, Qingjing

AU - Bian, Zhaoxiang

AU - Wang, Jun

N1 - Funding Information: We gratefully acknowledge financial support from the National Natural Science Foundation of China (NSFC 21971102) and Shenzhen Basic Research Program (JCYJ20170817112532779). Publisher copyright: © 2020 American Chemical Society

PY - 2020/4/3

Y1 - 2020/4/3

N2 - A highly efficient Rh(I)/(S)-xyl-Binap catalytic system is developed for the asymmetric hydroselenation of various nonpolar olefins with diselenides. Under these mild reaction conditions, a wide range of heterobicyclic alkenes give selenol-incorporated adducts in excellent enantioselectivities (up to 97%) along with high yields (up to 96%) by overcoming self-promoted racemic hydroselenation. The strategy is also applied for kinetic resolution of unsymmetric oxabenzonorbornadiene.

AB - A highly efficient Rh(I)/(S)-xyl-Binap catalytic system is developed for the asymmetric hydroselenation of various nonpolar olefins with diselenides. Under these mild reaction conditions, a wide range of heterobicyclic alkenes give selenol-incorporated adducts in excellent enantioselectivities (up to 97%) along with high yields (up to 96%) by overcoming self-promoted racemic hydroselenation. The strategy is also applied for kinetic resolution of unsymmetric oxabenzonorbornadiene.

UR - http://www.scopus.com/inward/record.url?scp=85082181747&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.0c00762

DO - 10.1021/acs.orglett.0c00762

M3 - Journal article

C2 - 32195590

AN - SCOPUS:85082181747

SN - 1523-7060

VL - 22

SP - 2781

EP - 2785

JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

Rhodium-Catalyzed Enantioselective Hydroselenation of Heterobicyclic Alkenes

Abstract

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