Highly Enantioselective Vinyl Additions of Vinylaluminum to Ketones Catalyzed by a Titanium(IV) Catalyst of (S)-BINOL
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...
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| Veröffentlicht in: | Organic letters 2009-02, Vol.11 (3), p.499-502 |
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| container_title | Organic letters |
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| creator | Biradar, Deepak Baburao Gau, Han-Mou |
| description | 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. |
| doi_str_mv | 10.1021/ol801999u |
| format | Article |
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| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2009-02, Vol.11 (3), p.499-502 |
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| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Alkynes - chemical synthesis Alkynes - chemistry Aluminum - chemistry Catalysis Combinatorial Chemistry Techniques Ketones - chemical synthesis Ketones - chemistry Molecular Structure Naphthols - chemistry Organometallic Compounds - chemistry Stereoisomerism Titanium - chemistry Vinyl Compounds - chemistry |
| title | Highly Enantioselective Vinyl Additions of Vinylaluminum to Ketones Catalyzed by a Titanium(IV) Catalyst of (S)-BINOL |
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