Tags

Type your tag names separated by a space and hit enter

Highly regioselective, catalytic asymmetric reductive coupling of 1,3-enynes and ketones.
Org Lett. 2005 Jul 07; 7(14):3077-80.OL

Abstract

[reaction: see text] Highly regioselective, catalytic asymmetric reductive coupling reactions of 1,3-enynes and ketones have been achieved using catalytic amounts of Ni(cod)(2) and a P-chiral, monodentate ferrocenyl phosphine ligand. These couplings represent the first examples of catalytic, intermolecular reductive coupling of alkynes and ketones, enantioselective or otherwise, and afford synthetically useful 1,3-dienes possessing a quaternary carbinol stereogenic center in up to 70% ee.

Authors+Show Affiliations

Miller KM
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, 02139, USA.
Jamison TF
No affiliation info available

MeSH

AlkynesCatalysisCombinatorial Chemistry TechniquesIndicators and ReagentsKetonesMolecular StructureOxidation-ReductionStereoisomerism

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
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

15987209

Citation

Miller, Karen M., and Timothy F. Jamison. "Highly Regioselective, Catalytic Asymmetric Reductive Coupling of 1,3-enynes and Ketones." Organic Letters, vol. 7, no. 14, 2005, pp. 3077-80.
Miller KM, Jamison TF. Highly regioselective, catalytic asymmetric reductive coupling of 1,3-enynes and ketones. Org Lett. 2005;7(14):3077-80.
Miller, K. M., & Jamison, T. F. (2005). Highly regioselective, catalytic asymmetric reductive coupling of 1,3-enynes and ketones. Organic Letters, 7(14), 3077-80.
Miller KM, Jamison TF. Highly Regioselective, Catalytic Asymmetric Reductive Coupling of 1,3-enynes and Ketones. Org Lett. 2005 Jul 7;7(14):3077-80. PubMed PMID: 15987209.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly regioselective, catalytic asymmetric reductive coupling of 1,3-enynes and ketones. AU - Miller,Karen M, AU - Jamison,Timothy F, PY - 2005/7/1/pubmed PY - 2006/4/28/medline PY - 2005/7/1/entrez SP - 3077 EP - 80 JF - Organic letters JO - Org Lett VL - 7 IS - 14 N2 - [reaction: see text] Highly regioselective, catalytic asymmetric reductive coupling reactions of 1,3-enynes and ketones have been achieved using catalytic amounts of Ni(cod)(2) and a P-chiral, monodentate ferrocenyl phosphine ligand. These couplings represent the first examples of catalytic, intermolecular reductive coupling of alkynes and ketones, enantioselective or otherwise, and afford synthetically useful 1,3-dienes possessing a quaternary carbinol stereogenic center in up to 70% ee. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/15987209/Highly_regioselective_catalytic_asymmetric_reductive_coupling_of_13_enynes_and_ketones_ DB - PRIME DP - Unbound Medicine ER -