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Borane-mediated aldol cycloreduction of monoenone monoketones: diastereoselective formation of quaternary centers.
J Org Chem. 2003 Jan 10; 68(1):11-4.JO

Abstract

Exposure of monoenone monoketones to catecholborane in THF at ambient temperature results in tandem 1,4-reduction-aldol cyclization. For aromatic and heteroaromatic enones, six-membered cyclic aldol products are formed in excellent yield with high levels of syn diastereoselectivity. Five-membered ring formation proceeds less readily, but the yield of cyclized product is improved through introduction of Rh(I) salts.

Authors+Show Affiliations

Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, USA.No affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

12515454

Citation

Huddleston, Ryan R., et al. "Borane-mediated Aldol Cycloreduction of Monoenone Monoketones: Diastereoselective Formation of Quaternary Centers." The Journal of Organic Chemistry, vol. 68, no. 1, 2003, pp. 11-4.
Huddleston RR, Cauble DF, Krische MJ. Borane-mediated aldol cycloreduction of monoenone monoketones: diastereoselective formation of quaternary centers. J Org Chem. 2003;68(1):11-4.
Huddleston, R. R., Cauble, D. F., & Krische, M. J. (2003). Borane-mediated aldol cycloreduction of monoenone monoketones: diastereoselective formation of quaternary centers. The Journal of Organic Chemistry, 68(1), 11-4.
Huddleston RR, Cauble DF, Krische MJ. Borane-mediated Aldol Cycloreduction of Monoenone Monoketones: Diastereoselective Formation of Quaternary Centers. J Org Chem. 2003 Jan 10;68(1):11-4. PubMed PMID: 12515454.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Borane-mediated aldol cycloreduction of monoenone monoketones: diastereoselective formation of quaternary centers. AU - Huddleston,Ryan R, AU - Cauble,David F, AU - Krische,Michael J, PY - 2003/1/8/pubmed PY - 2003/6/21/medline PY - 2003/1/8/entrez SP - 11 EP - 4 JF - The Journal of organic chemistry JO - J Org Chem VL - 68 IS - 1 N2 - Exposure of monoenone monoketones to catecholborane in THF at ambient temperature results in tandem 1,4-reduction-aldol cyclization. For aromatic and heteroaromatic enones, six-membered cyclic aldol products are formed in excellent yield with high levels of syn diastereoselectivity. Five-membered ring formation proceeds less readily, but the yield of cyclized product is improved through introduction of Rh(I) salts. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/12515454/Borane_mediated_aldol_cycloreduction_of_monoenone_monoketones:_diastereoselective_formation_of_quaternary_centers_ L2 - https://doi.org/10.1021/jo020629f DB - PRIME DP - Unbound Medicine ER -