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Highly enantioselective phenylacetylene additions to ketones catalyzed by (S)-BINOL-Ti complex.
Org Lett. 2004 Nov 11; 6(23):4147-9.OL

Abstract

The readily available and inexpensive (S)-BINOL ligand in combination with Ti(O(i)Pr)(4) is an effective chiral catalyst for the catalytic asymmetric addition of alkynylzinc to unactivated simple ketones. Good to excellent enantioselectivities were achieved. No previous case has been reported successfully using BINOL to catalyze the addition of phenylacetylene to unactivated ketones, and thus the utility of BINOL in asymmetric catalysis is expanded.

Authors+Show Affiliations

Zhou Y
Department of Biochemistry & Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou 730000, China.
Wang R
No affiliation info available
Xu Z
No affiliation info available
Yan W
No affiliation info available
Liu L
No affiliation info available
Kang Y
No affiliation info available
Han Z
No affiliation info available

MeSH

AcetyleneCatalysisKetonesNaphtholsStereoisomerismTitanium

Pub Type(s)

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

Language

eng

PubMed ID

15524429

Citation

Zhou, Yifeng, et al. "Highly Enantioselective Phenylacetylene Additions to Ketones Catalyzed By (S)-BINOL-Ti Complex." Organic Letters, vol. 6, no. 23, 2004, pp. 4147-9.
Zhou Y, Wang R, Xu Z, et al. Highly enantioselective phenylacetylene additions to ketones catalyzed by (S)-BINOL-Ti complex. Org Lett. 2004;6(23):4147-9.
Zhou, Y., Wang, R., Xu, Z., Yan, W., Liu, L., Kang, Y., & Han, Z. (2004). Highly enantioselective phenylacetylene additions to ketones catalyzed by (S)-BINOL-Ti complex. Organic Letters, 6(23), 4147-9.
Zhou Y, et al. Highly Enantioselective Phenylacetylene Additions to Ketones Catalyzed By (S)-BINOL-Ti Complex. Org Lett. 2004 Nov 11;6(23):4147-9. PubMed PMID: 15524429.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly enantioselective phenylacetylene additions to ketones catalyzed by (S)-BINOL-Ti complex. AU - Zhou,Yifeng, AU - Wang,Rui, AU - Xu,Zhaoqing, AU - Yan,Wenjin, AU - Liu,Lei, AU - Kang,Yongfeng, AU - Han,Zhijian, PY - 2004/11/5/pubmed PY - 2006/2/8/medline PY - 2004/11/5/entrez SP - 4147 EP - 9 JF - Organic letters JO - Org Lett VL - 6 IS - 23 N2 - The readily available and inexpensive (S)-BINOL ligand in combination with Ti(O(i)Pr)(4) is an effective chiral catalyst for the catalytic asymmetric addition of alkynylzinc to unactivated simple ketones. Good to excellent enantioselectivities were achieved. No previous case has been reported successfully using BINOL to catalyze the addition of phenylacetylene to unactivated ketones, and thus the utility of BINOL in asymmetric catalysis is expanded. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/15524429/Highly_enantioselective_phenylacetylene_additions_to_ketones_catalyzed_by__S__BINOL_Ti_complex_ DB - PRIME DP - Unbound Medicine ER -