Rhodium-Catalyzed, Enantioselective Hydroacylation of ortho-Allylbenzaldehydes | Zendy

Kirsten F. Johnson | Zendy; Adam C. Schmidt | Zendy; Levi M. Stanley | Zendy

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Rhodium-Catalyzed, Enantioselective Hydroacylation of ortho-Allylbenzaldehydes

Author(s) -

Kirsten F. Johnson,

Adam C. Schmidt,

Levi M. Stanley

Publication year - 2015

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.5b02559

Subject(s) - hydroacylation , rhodium , enantioselective synthesis , chemistry , catalysis , isomerization , alkene , norbornadiene , dehydration , organic chemistry , biochemistry

The development of a rhodium catalyst for endo- and enantioselective hydroacylation of ortho-allylbenzaldehydes is reported. A catalyst generated in situ from [Rh(COD)Cl]2, (R)-DTBM-SEGPHOS, and NaBARF promotes the desired hydroacylation reactions and minimizes the formation of byproducts from competitive alkene isomerization and ene/dehydration pathways. These rhodium-catalyzed processes generate the 3,4-dihydronaphthalen-1(2H)-one products in moderate-to-high yields (49-91%) with excellent enantioselectivities (96-99% ee).

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