Cobalt‐Catalyzed Enantioselective Alkenylation of Aldehydes

Catalytic enantioselective alkenylation of aldehydes with easily accessible alkenyl halides promoted by a chiral cobalt complex derived from a newly developed tridentate bisoxazolinephosphine is presented. Such processes represent an unprecedented reaction pathway for cobalt catalysis and a general...

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Bibliographic Details
Published inAngewandte Chemie Vol. 136; no. 33
Main Authors Lin, Chuiyi, Zhang, Jiwu, Sun, Zhao, Guo, Yinlong, Chong, Qinglei, Zhang, Zhihan, Meng, Fanke
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 12.08.2024
Subjects
Alcohols
Aldehydes
alkenylation
allylic alcohol
axial stereogenicity
Catalysis
Cobalt
Cobalt compounds
Enantiomers
enantioselective catalysis
Halides
Reagents
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Summary:Catalytic enantioselective alkenylation of aldehydes with easily accessible alkenyl halides promoted by a chiral cobalt complex derived from a newly developed tridentate bisoxazolinephosphine is presented. Such processes represent an unprecedented reaction pathway for cobalt catalysis and a general approach that enable rapid construction of highly diversified enantioenriched allylic alcohols containing a 1,1‐, 1,2‐disubstituted and trisubstituted alkene as well as axial stereogenicity in up to 99 % yield and 99 : 1 er without the need of preformation of alkenyl–metal reagents. DFT calculations revealed the origin of enantioselectivity. A new approach for highly efficient and enantioselective alkenylation of aldehydes promoted by an easily accessible cobalt‐based complex was developed. This protocol represents the first example of incorporating a wide range of alkenyl groups with diversified substitution patterns as well as axial stereogenicity into enantioenriched allylic alcohols.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202405290