Structure‐Reactivity Studies of Simple 4‐Hydroxyprolinamide Organocatalysts in the Asymmetric Michael Addition Reaction of Aldehydes to Nitroolefins | Zendy

Watts John | Zendy; Luu Lien | Zendy; McKee Vickie | Zendy; Carey Ed | Zendy; Kelleher Fintan | Zendy

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Structure‐Reactivity Studies of Simple 4‐Hydroxyprolinamide Organocatalysts in the Asymmetric Michael Addition Reaction of Aldehydes to Nitroolefins

Author(s) -

Watts John,

Luu Lien,

McKee Vickie,

Carey Ed,

Kelleher Fintan

Publication year - 2012

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201100028

Subject(s) - chemistry , michael reaction , conjugate , aldehyde , reactivity (psychology) , catalysis , organocatalysis , organic chemistry , addition reaction , enantioselective synthesis , medicine , mathematical analysis , alternative medicine , mathematics , pathology

A series of simple 4‐hydroxyprolinamides was synthesised and they were found to act as organocatalysts for the asymmetric conjugate addition of aldehydes to nitroolefins in excellent yields (98%), with complete diastereoselectivity (99:1, syn:anti ) and enantioselectivity (98% ee for syn ). Furthermore, the use of low catalyst loadings (5 mol%) and a low aldehyde molar excess (1.5 equivalents) were achieved.

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