- Cycloadditions of siloxy alkynes with 1,2-diazines: From reaction discovery to identification of an antiglycolytic chemotype
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Cycloaddition uncovered: The title reaction produces novel polycyclic compounds with high efficiency and excellent diastereoselectivity under mild reaction conditions. A small-molecule library, synthesized using this reaction, yielded a novel chemotype which inhibited glycolytic ATP production by blocking glucose uptake in CHO-K1 cells. DMF=N,N-dimethylformamide, Tf= trifluoromethanesulfonyl, TIPS=triisopropylsilyl. Copyright
- Montavon, Timothy J.,Tuerkmen, Yunus E.,Shamsi, Noumaan A.,Miller, Christopher,Sumaria, Chintan S.,Rawal, Viresh H.,Kozmin, Sergey A.
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supporting information
p. 13576 - 13579
(2014/01/06)
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- Silver-catalyzed aldehyde olefination using siloxyalkynes
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We describe the development of a silvercatalyzed carbonyl olefination employing electronrich siloxyalkynes. This process constitutes an efficient synthesis of trisubstituted unsaturated esters, and represents an alternative to the widely utilized Horner-Wadsworth-Emmons reaction. Excellent diastereoselectivities are observed for a range of aldehydes using either 1-siloxy-l-propyne or 1-siloxy1-hexyne. This mild catalytic process also enables chemoselective olefination of aldehydes in the presence of either ester or ketone functionality. Furthermore, since no by-products are generated, this catalytic process is perfectly suited for development of sequential reactions that can be carried out in a single flask.
- Sun, Jianwei,Keller, Valerie A.,Meyer, S. Todd,Kozmin, Sergey A.
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supporting information; experimental part
p. 839 - 842
(2010/06/19)
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- Silver-catalyzed hydroamination of siloxy alkynes
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(Chemical Equation Presented) New catalytic process: The silver-catalyzed hydroamination of siloxy alkynes with secondary amides furnishes silyl ketene aminals with high efficiency and excellent diastereoselectivity (see scheme), including some that are unavailable by conventional silylation methods. The reaction comprises a fast and reversible silver-alkyne complexation, followed by a rate-determining C-N bond-forming step.
- Sun, Jianwei,Kozmin, Sergey A.
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p. 4991 - 4993
(2007/10/03)
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- Trisubstituted Olefins via Ester-Derived (Silyloxy)acetylenes: A Highly Stereoselective Alternative to the Horner-Wadsworth-Emmons Reaction
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Crude ((triisopropylsilyl)oxy)acetylenes 2, prepared in one step from common esters 1, react with aldehydes in 60-65 percent overall yield after methanol quench to afford α,β-unsaturated esters 3 with very high E/Z stereoselectivity.
- Kowalski, Conrad J.,Sakdarat, Santi
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p. 1977 - 1979
(2007/10/02)
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- TRIALKYLSILYLOXYALKINES: SYNTHESIS AND AROMATIC ANNULATION REACTIONS
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Substitued resorcinols are produced by the thermal addition of cyclobutenones to trialkylsilyloxyalkines.The dehydrobromination of (Z)-2-bromovinyl silyl ethers has been employed in the first synthesis of trialkylsilyloxyethyne derivatives.
- Danheiser, Rick L.,Nishida, Atsushi,Savariar, Selvaraj,Trova, Michael P.
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p. 4917 - 4920
(2007/10/02)
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