Zinc Radical Transfer Based Modular Approach to Enantiopure Alkylidene‐β‐prolines from  N ‐( tert ‐Butylsulfinyl)‐α‐(aminomethyl)acrylates | Zendy

Beniazza Redouane | Zendy; Romain Elise | Zendy; Chemla Fabrice | Zendy; Ferreira Franck | Zendy; Jackowski Olivier | Zendy; PerezLuna Alejandro | Zendy

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Zinc Radical Transfer Based Modular Approach to Enantiopure Alkylidene‐β‐prolines from N ‐( tert ‐Butylsulfinyl)‐α‐(aminomethyl)acrylates

Author(s) -

Beniazza Redouane,

Romain Elise,

Chemla Fabrice,

Ferreira Franck,

Jackowski Olivier,

PerezLuna Alejandro

Publication year - 2015

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201501173

Subject(s) - enantiopure drug , chemistry , trifluoromethanesulfonate , zinc , adduct , electrophile , medicinal chemistry , radical cyclization , stereochemistry , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis

N ‐( tert ‐Butylsulfinyl)‐α‐(aminomethyl)acrylates with tethered silylated alkynes undergo a tandem 1,4‐addition/carbozincation reaction upon exposure to dialkylzinc compounds in the presence of air. The process follows a zinc‐radical‐transfer mechanism and provides vinylzinc adducts that can react subsequently with electrophiles. High levels of chiral induction ( dr > 90:10) from the tert ‐butylsulfinyl directing group are achieved during the radical 5‐ exo ‐ dig cyclization by adding samarium(III) triflate. The sequence overall provides straightforward modular access to enantiopure ( E )‐4‐alkylidene‐β‐prolines from tert ‐butanesulfinamide.

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