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Highly enantioselective vinyl additions of vinylaluminum to ketones catalyzed by a titanium(IV) catalyst of (S)-BINOL.
Org Lett. 2009 Feb 05; 11(3):499-502.OL

Abstract

We report a novel asymmetric addition of vinyl group to ketones using vinylaluminum reagents catalyzed by in situ prepared Ti(O(i)Pr)(4) complexes of (S)-BINOL to afford diversified tertiary allylic alochols. Varieties of aromatic ketones bearing either an electron-donating or an electron-withdrawing substituent on the aromatic ring were examined to afford products in excellent enantioselectivities of up to 98% ee with high yields. A 10-fold scale-up reaction afforded the product in a similar yield with a comparable enantioselectivity. More importantly, additions of a variety of vinyl reagents including functionalized vinyls were demonstrated, affording tertiary allylic alcohols with good to excellent enantioselectivities of up to 96% ee.

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Authors+Show Affiliations

Biradar DB
Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan.
Gau HM
No affiliation info available

MeSH

AlkynesAluminumCatalysisCombinatorial Chemistry TechniquesKetonesMolecular StructureNaphtholsOrganometallic CompoundsStereoisomerismTitaniumVinyl Compounds

Pub Type(s)

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

Language

eng

PubMed ID

19117491

Citation

Biradar, Deepak Baburao, and Han-Mou Gau. "Highly Enantioselective Vinyl Additions of Vinylaluminum to Ketones Catalyzed By a titanium(IV) Catalyst of (S)-BINOL." Organic Letters, vol. 11, no. 3, 2009, pp. 499-502.
Biradar DB, Gau HM. Highly enantioselective vinyl additions of vinylaluminum to ketones catalyzed by a titanium(IV) catalyst of (S)-BINOL. Org Lett. 2009;11(3):499-502.
Biradar, D. B., & Gau, H. M. (2009). Highly enantioselective vinyl additions of vinylaluminum to ketones catalyzed by a titanium(IV) catalyst of (S)-BINOL. Organic Letters, 11(3), 499-502. https://doi.org/10.1021/ol801999u
Biradar DB, Gau HM. Highly Enantioselective Vinyl Additions of Vinylaluminum to Ketones Catalyzed By a titanium(IV) Catalyst of (S)-BINOL. Org Lett. 2009 Feb 5;11(3):499-502. PubMed PMID: 19117491.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly enantioselective vinyl additions of vinylaluminum to ketones catalyzed by a titanium(IV) catalyst of (S)-BINOL. AU - Biradar,Deepak Baburao, AU - Gau,Han-Mou, PY - 2009/1/2/entrez PY - 2009/1/2/pubmed PY - 2009/2/27/medline SP - 499 EP - 502 JF - Organic letters JO - Org. Lett. VL - 11 IS - 3 N2 - We report a novel asymmetric addition of vinyl group to ketones using vinylaluminum reagents catalyzed by in situ prepared Ti(O(i)Pr)(4) complexes of (S)-BINOL to afford diversified tertiary allylic alochols. Varieties of aromatic ketones bearing either an electron-donating or an electron-withdrawing substituent on the aromatic ring were examined to afford products in excellent enantioselectivities of up to 98% ee with high yields. A 10-fold scale-up reaction afforded the product in a similar yield with a comparable enantioselectivity. More importantly, additions of a variety of vinyl reagents including functionalized vinyls were demonstrated, affording tertiary allylic alcohols with good to excellent enantioselectivities of up to 96% ee. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/19117491/Highly_enantioselective_vinyl_additions_of_vinylaluminum_to_ketones_catalyzed_by_a_titanium_IV__catalyst_of__S__BINOL_ L2 - https://dx.doi.org/10.1021/ol801999u DB - PRIME DP - Unbound Medicine ER -