Highly Stereoselective Synthesis of Substituted γ-Lactams from Acylsilanes

It takes three: The stereoselective synthesis of highly substituted γ‐lactams from amide enolates, acylsilanes, and imines is reported. This multicomponent reaction accesses γ‐amino‐β‐hydroxy amides in a single flask with good yields and excellent levels of diastereoselectivity (see scheme). Exposur...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2008-03, Vol.47 (12), p.2294-2297
Main Authors: Lettan, Robert B. II, Woodward, Chase C, Scheidt, Karl A
Format: Article
Language:English
Subjects:
Acylation
acylsilanes
Amides - chemistry
Amination
chiral auxiliaries
homoenolates
Hydroxylation
Lactams - chemical synthesis
Lactams - chemistry
Models, Chemical
Molecular Structure
Silanes - chemistry
Stereoisomerism
synthetic methods
γ-lactams
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Summary:It takes three: The stereoselective synthesis of highly substituted γ‐lactams from amide enolates, acylsilanes, and imines is reported. This multicomponent reaction accesses γ‐amino‐β‐hydroxy amides in a single flask with good yields and excellent levels of diastereoselectivity (see scheme). Exposure of the linear products to microwave irradiation and acidic conditions promotes a cyclization to form the corresponding γ‐lactams in excellent yields.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200705229