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Catalytic asymmetric addition of alkylzinc and functionalized alkylzinc reagents to ketones.
J Org Chem. 2005 Jan 21; 70(2):448-55.JO

Abstract

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%.

Authors+Show Affiliations

Jeon SJ
P. Roy and Diana T. Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.
Li H
No affiliation info available
García C
No affiliation info available
LaRochelle LK
No affiliation info available
Walsh PJ
No affiliation info available

MeSH

AlcoholsCatalysisCrystallography, X-RayKetonesMolecular StructureOrganometallic CompoundsStereoisomerismZinc

Pub Type(s)

Journal Article
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

15651785

Citation

Jeon, Sang-Jin, et al. "Catalytic Asymmetric Addition of Alkylzinc and Functionalized Alkylzinc Reagents to Ketones." The Journal of Organic Chemistry, vol. 70, no. 2, 2005, pp. 448-55.
Jeon SJ, Li H, García C, et al. Catalytic asymmetric addition of alkylzinc and functionalized alkylzinc reagents to ketones. J Org Chem. 2005;70(2):448-55.
Jeon, S. J., Li, H., García, C., LaRochelle, L. K., & Walsh, P. J. (2005). Catalytic asymmetric addition of alkylzinc and functionalized alkylzinc reagents to ketones. The Journal of Organic Chemistry, 70(2), 448-55.
Jeon SJ, et al. Catalytic Asymmetric Addition of Alkylzinc and Functionalized Alkylzinc Reagents to Ketones. J Org Chem. 2005 Jan 21;70(2):448-55. PubMed PMID: 15651785.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic asymmetric addition of alkylzinc and functionalized alkylzinc reagents to ketones. AU - Jeon,Sang-Jin, AU - Li,Hongmei, AU - García,Celina, AU - LaRochelle,Lynne K, AU - Walsh,Patrick J, PY - 2005/1/18/pubmed PY - 2005/3/23/medline PY - 2005/1/18/entrez SP - 448 EP - 55 JF - The Journal of organic chemistry JO - J Org Chem VL - 70 IS - 2 N2 - 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%. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/15651785/Catalytic_asymmetric_addition_of_alkylzinc_and_functionalized_alkylzinc_reagents_to_ketones_ DB - PRIME DP - Unbound Medicine ER -