Enantioselective Synthesis of Allylic Sulfones via Rhodium-Catalyzed Direct Hydrosulfonylation of Allenes and Alkynes.
J Am Chem Soc
; 146(25): 16996-17002, 2024 Jun 26.
Article
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| MEDLINE
| ID: mdl-38875709
ABSTRACT
A highly regio- and enantioselective hydrosulfonylation using commercially available sodium sulfinates is reported, providing the first direct asymmetric rhodium-catalyzed hydrosulfonylation of allenes/alkynes to synthesize chiral allylic sulfones. Ligand screening studies demonstrated the indispensable role of the C1-symmetric P,N-ligand (Rax,S,S)-StackPhim for achieving both high regioselecitivity (>201) and enantioselectivity (up to 97% ee). Notably, the operationally simple method and mild conditions allow for the rapid preparation of chiral allylic sulfones with a wide scope of functional groups. Moreover, the use of sodium tert-butyldimethylsilyloxymethanesulfinate enables the collective synthesis of various chiral sulfone derivatives after simple transformations of the protected hydroxymethyl product.
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MEDLINE
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En
Revista:
J Am Chem Soc
Año:
2024
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Article
País de afiliación:
Estados Unidos