182210-51-1Relevant articles and documents
New access to chiral syn-α-Chlorohydrins and cis-vinyloxiranes through chloroallyboration
Jayaraman, Seetharaman
, p. 4765 - 4768 (1995)
A new method to generate chiral cis-vinyloxiranes from readily available starting materials is reported. (X-Chloroallyl)lithium, generated in situ from LiN(c-Hex)2 and allyl chloride at -95°C, reacts with (-)-β-methoxydiisopinocampheylborane,
Sulfur-ylide-mediated synthesis of functionalized and trisubstituted epoxides with high enantioselectivity; Application to the synthesis of CDP-840
Aggarwal, Varinder K.,Bae, Imhyuck,Lee, Hee-Yoon,Richardson, Jeffery,Williams, David T.
, p. 3274 - 3278 (2007/10/03)
Benzyl and substituted allyl sulfonium salts react with a broad range of simple and functionalized aldehydes and ketones to give epoxides with high diastereoselectivity and high enantioselectivity (see scheme). The process has been applied to a short synthesis of the phosphodiesterase-IV inhibitor CDP-840. R1, R2 = hydrogen, alkyl, alkenyl, alkynyl, aryl, or pyridyl.