Triethoxysilyl acetylene

Triethoxysilyl acetylene (51) allows a new organocatalytic approach toward the introduction of the alkyne moiety via a nucleophilic addition to aromatic aldehydes, ketones, and aldimines, with EtOK as catalyst (10 mol%). Although a catalytic asymmetric version has not yet been developed, the application of a chiral auxiliary, in the case of imines 53 (Scheme 7.9), led to an impressively high dia-stereoselectivity (20 1) [54], unparalleled by other acetylenic organometallics. 

The hydrosilylation of 1-hexene (28) with triethoxysilane (29) in the presence of a poly-y-mercaptopropylsiloxane platinum complex leads to hexyltriethoxysilane (30) (equation 16), whereas the hydrosilylation of acetylene (31) can afford both the mono- and disilylated product, i.e. vinyltriethoxysilane (32) and l,2-bis(triethoxysilyl)ethane (33) respectively (equation 17)34. 

Diels-Alder reactions 47 triethoxysilyl acetylene 395 triethylamine (TEA) 721 triflate salts 1095 triflimides 436... 

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