17922-24-6Relevant articles and documents
Stereoselective Synthesis of Z-α,β-Unsaturated Sulfones Using Peterson Reagents
Ando, Kaori,Wada, Tomohiro,Okumura, Miho,Sumida, Hiroshi
supporting information, p. 6026 - 6029 (2016/01/09)
New Peterson reagents were prepared by introducing alkyloxy groups on the silicon atom in order to fix the conformation of the sulfone anion. The reagents 1d and 1e reacted with a variety of aldehydes after the treatment with Li-base to give Z-α,β-unsaturated sulfones with up to >99:1 selectivity in good to excellent yields. For the reaction with aliphatic aldehydes, CPME (cyclopentyl methyl ether) is the choice of solvent, while DME (1,2-dimethoxyethane) gave higher selectivity for the reaction with aromatic aldehydes.
Highly (Z)-selective synthesis of β-monosubstituted α,β-unsaturated cyanides using the peterson reaction
Kojima, Satoshi,Fukuzaki, Tomohide,Yamakawa, Atsushi,Murai, Yutaka
, p. 3917 - 3920 (2007/10/03)
(Chemical Equation Presented) The Peterson reaction between (t-BuO)Ph 2SiCH2CN and various aldehydes furnishes the corresponding β-monosubstituted α,β-unsaturated cyanides with high Z selectivity (Z:E = 92:8 to >98:2).
Symmetrical Alkoxysilyl Ethers. A New Class of Alcohol-Protecting Groups. Preparation of tert-Butoxydiphenylsilyl Ethers
Gillard, John W.,Fortin, Rejean,Morton, Howard E.,Yoakim, Christiane,Quesnelle, Claude A.,at al.
, p. 2602 - 2608 (2007/10/02)
The preparation and evaluation of a new class of alcohol-protecting groups, the alkoxydiphenylsilyl ethers, are described.In particular, tert-butoxydiphenylsilyl ethers, which can be formed from primary, secondary, or tertiary alcohols and tert-butoxydiphenylsilyl chloride, offer the useful synthetic properties of acid stability and high fluoride reactivity.Opportunities for selective silyl group cleavage are highlighted.
