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Highly Enantio- and Diastereoselective Organocatalytic Domino Michael-Aldol Reactions of β-Diketone and β-Ketosulfone Nucleophiles with α,β-Unsaturated Ketones

✍ Scribed by Juha Pulkkinen; Pompiliu S. Aburel; Nis Halland; Karl Anker Jørgensen

Publisher: John Wiley and Sons
Year: 2004
Tongue: English
Weight: 97 KB
Volume: 346
Category: Article
ISSN: 1615-4150
DOI: 10.1002/adsc.200404115

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✦ Synopsis

Abstract

A chiral imidazolidine catalyst was shown to catalyze the highly enantio‐ and diastereoselective domino Michael‐aldol reaction of β‐diketone and β‐ketosulfone derivatives with α,β‐unsaturated ketones to form optically active cyclohexanones having three or four contiguous chiral centers. The Michael‐aldol adducts were formed as single diastereomers in up 99% ee.

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