Catalytic Asymmetric Addition of Alkylzinc and Functionalized Alkylzinc Reagents to Ketones

We describe our full report of the catalytic asymmetric addition of simple and functionalized dialkylzinc reagents to a broad range of saturated ketones and enones. The functionalized organozinc reagents contain esters, silyl ethers, alkyl chlorides, and alkyl bromides. In general, the resulting ter...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-01, Vol.70 (2), p.448-455
Main Authors: Jeon, Sang-Jin, Li, Hongmei, García, Celina, LaRochelle, Lynne K, Walsh, Patrick J
Format: Article
Language:English
Subjects:
Alcohols - chemical synthesis
Alcohols - chemistry
Catalysis
Catalysts: preparations and properties
Chemistry
Crystallography, X-Ray
Exact sciences and technology
General and physical chemistry
Ketones - chemistry
Kinetics and mechanisms
Molecular Structure
Organic chemistry
Organometallic Compounds - chemistry
Reactivity and mechanisms
Stereoisomerism
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Zinc - chemistry
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Summary:We describe our full report of the catalytic asymmetric addition of simple and functionalized dialkylzinc reagents to a broad range of saturated ketones and enones. The functionalized organozinc reagents contain esters, silyl ethers, alkyl chlorides, and alkyl bromides. In general, the resulting tertiary alcohol products are isolated with high ee's. With some substrates, yields are low as a result of the formation of aldol byproducts. Most substrates undergo additions with good yields reaching as high as 91%.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo048683e