73795-12-7Relevant academic research and scientific papers
Switching regioselectivity in the allylation of imines by N-side chain tuning
Delaye, Pierre-Olivier,Vasse, Jean-Luc,Szymoniak, Jan
supporting information; experimental part, p. 3004 - 3007 (2012/08/14)
A spectacular inversion of α- to γ-regioselectivity in the allylzincation of imines can be achieved by fine-tuning of the N-side chain. This approach allows easy preparation of regioisomeric amines, in racemic as well as enantiopure forms. The usefulness of the method is illustrated by the parallel asymmetric syntheses of 2,3- and 2,5-diphenylpyrrolidines.
Iodine-promoted silylation of alcohols with silyl chlorides. Synthetic and mechanistic studies
Bartoszewicz, Agnieszka,Kalek, Marcin,Stawinski, Jacek
, p. 8843 - 8850 (2008/12/21)
An efficient silylating system for 1°, 2°, and 3° alcohols, consisting of a silyl chloride/N-methylimidazole/iodine, was developed. Synthetic and mechanistic aspects of this new reagent system, and particularly the role of iodine were investigated in detail using 1H NMR spectroscopy.
A convenient and versatile method for the preparation of α-hydroxymethyl ketone derivatives from the corresponding allyl silyl ethers or allyl carboxylates
Hon, Yung-Son,Wong, Ying-Chieh,Wu, Kuo-Jui
experimental part, p. 896 - 914 (2009/12/06)
The ozonolysis of 1-substituted allyl silyl ethers or 1-substituted allyl carboxylates followed by treatment with bases gave the corresponding α-silyloxymethyl- or α-acyloxymethyl-ketones in good yields. It is proposed to proceed via the corresponding α-silyloxy- or α-acyloxyaldehydes intermediates followed by 1,4-group migration. The results of theoretical calculations are applicable to explain the experimental results.
Regio- and stereospecific formation of protected allylic alcohols via zirconium-mediated SN2′ substitution of allylic chlorides
Fox, Richard J.,Lalic, Gojko,Bergman, Robert G.
, p. 14144 - 14145 (2008/09/18)
A new, highly regio- and stereospecific SN2′ substitution reaction between a zirconium oxo complex and allylic chloride has been achieved. The resulting allylic alcohol or TBS-protected allylic ether products were isolated in good to excellent yields with a wide range of E-allylic chlorides. A mechanism for the SN2′ allylic substitution consistent with kinetic, stereochemical, and secondary isotope effect studies was proposed. Copyright
Highly Diastereoselective Conjugate Addition of Lithium Dialkylamides to α,β-Unsaturated Esters Having a Chiral Center at the γ-Position
Asao, Naoki,Shimada, Takashi,Sudo, Tomoko,Tsukada, Naofumi,Yazawa, Kazuhiko,Gyoung, Young Soo,Uyehara, Tadao,Yamamoto, Yoshinori
, p. 6274 - 6282 (2007/10/03)
The conjugate addition of lithium amides 2 to tert-butyl 4-(OR)-substituted-2-pentenoates 1 produced a mixture of the syn- and anrt-amino esters (3 and 4) in high yields. Sterically bulky OR groups, such as trityloxy and tert-butyldiphenylsilyloxy, gave t
