Enantioselective Synthesis of Quaternary Δ 4 ‐ and Δ 5 ‐Dehydroprolines Based on a Two‐Step Formal [3+2] Cycloaddition of α‐Aryl and α‐Alkyl Isocyano(thio)acetates with Vinyl Ketones | Zendy

Odriozola Amaiur | Zendy; Oiarbide Mikel | Zendy; Palomo Claudio | Zendy

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Enantioselective Synthesis of Quaternary Δ 4 ‐ and Δ 5 ‐Dehydroprolines Based on a Two‐Step Formal [3+2] Cycloaddition of α‐Aryl and α‐Alkyl Isocyano(thio)acetates with Vinyl Ketones

Author(s) -

Odriozola Amaiur,

Oiarbide Mikel,

Palomo Claudio

Publication year - 2017

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201703526

Subject(s) - stereocenter , thio , enantioselective synthesis , bifunctional , aryl , chemistry , alkyl , squaramide , conjugate , catalysis , medicinal chemistry , organic chemistry , organocatalysis , mathematical analysis , mathematics

A divergent synthesis of optically active quaternary Δ 4 ‐ and Δ 5 ‐dehydro prolines is developed based on the first catalytic enantioselective conjugate addition of α‐substituted isocyano(thio)acetates to vinyl ketones that is general for both α‐aryl and α‐alkyl isocyano(thio)acetates. The new tetrasubstituted C−N stereocenter is formed without the need of any metal salt due to a bifunctional tertiary amine/squaramide catalyst, featuring a bulky polyaryl sidearm and an unusually short squaramide diamide H⋅⋅⋅H interatomic distance in the solid state.

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