Tags

Type your tag names separated by a space and hit enter

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.

Authors+Show Affiliations

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

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 -