Hydrogen-mediated aldol reductive coupling of vinyl ketones catalyzed by rhodium: high syn-selectivity through the effect of tri-2-furylphosphine.Org Lett. 2006 Feb 02; 8(3):519-22.OL
Abstract
[reaction: see text]. Catalytic hydrogenation of methyl vinyl ketone (MVK) and ethyl vinyl ketone (EVK) in the presence of diverse aldehydes at ambient temperature and pressure using tri-2-furylphosphine-ligated rhodium catalysts enables formation of aldol products with high levels of syn-diastereoselectivity. A progressive increase in diastereoselectivity is observed upon sequential replacement of phenyl residues for 2-furyl residues (Ph3P, FurPh2P, Fur2PhP, Fur3P). Hydrogen-labile functional groups, including alkynes, alkenes, benzylic ethers, and nitroarenes, remain intact under the coupling conditions.
Links
MeSH
Pub Type(s)
Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Language
eng
PubMed ID
16435874
Citation
Jung, Cheol-Kyu, et al. "Hydrogen-mediated Aldol Reductive Coupling of Vinyl Ketones Catalyzed By Rhodium: High Syn-selectivity Through the Effect of Tri-2-furylphosphine." Organic Letters, vol. 8, no. 3, 2006, pp. 519-22.
Jung CK, Garner SA, Krische MJ. Hydrogen-mediated aldol reductive coupling of vinyl ketones catalyzed by rhodium: high syn-selectivity through the effect of tri-2-furylphosphine. Org Lett. 2006;8(3):519-22.
Jung, C. K., Garner, S. A., & Krische, M. J. (2006). Hydrogen-mediated aldol reductive coupling of vinyl ketones catalyzed by rhodium: high syn-selectivity through the effect of tri-2-furylphosphine. Organic Letters, 8(3), 519-22.
Jung CK, Garner SA, Krische MJ. Hydrogen-mediated Aldol Reductive Coupling of Vinyl Ketones Catalyzed By Rhodium: High Syn-selectivity Through the Effect of Tri-2-furylphosphine. Org Lett. 2006 Feb 2;8(3):519-22. PubMed PMID: 16435874.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Hydrogen-mediated aldol reductive coupling of vinyl ketones catalyzed by rhodium: high syn-selectivity through the effect of tri-2-furylphosphine.
AU - Jung,Cheol-Kyu,
AU - Garner,Susan A,
AU - Krische,Michael J,
PY - 2006/1/27/pubmed
PY - 2006/10/19/medline
PY - 2006/1/27/entrez
SP - 519
EP - 22
JF - Organic letters
JO - Org Lett
VL - 8
IS - 3
N2 - [reaction: see text]. Catalytic hydrogenation of methyl vinyl ketone (MVK) and ethyl vinyl ketone (EVK) in the presence of diverse aldehydes at ambient temperature and pressure using tri-2-furylphosphine-ligated rhodium catalysts enables formation of aldol products with high levels of syn-diastereoselectivity. A progressive increase in diastereoselectivity is observed upon sequential replacement of phenyl residues for 2-furyl residues (Ph3P, FurPh2P, Fur2PhP, Fur3P). Hydrogen-labile functional groups, including alkynes, alkenes, benzylic ethers, and nitroarenes, remain intact under the coupling conditions.
SN - 1523-7060
UR - https://www.unboundmedicine.com/medline/citation/16435874/Hydrogen_mediated_aldol_reductive_coupling_of_vinyl_ketones_catalyzed_by_rhodium:_high_syn_selectivity_through_the_effect_of_tri_2_furylphosphine_
L2 - https://doi.org/10.1021/ol052859x
DB - PRIME
DP - Unbound Medicine
ER -