Stereocontrolled reactions mediated by remote sulfoxides: Formation and reactivity of enantiomerically pure benzylic centers

Autor:	Ana M. Martin Castro, Garcia Ruano Jose Luis Garcia Ruano Jose Luis
Rok vydání:	2007
Předmět:	Steric effects chemistry.chemical_classification Heteroatom Halide General Medicine General Chemistry Toluene Medicinal chemistry chemistry.chemical_compound chemistry Electrophile Organic chemistry Reactivity (chemistry) Alkyl
Zdroj:	Heteroatom Chemistry. 18:537-548
ISSN:	1098-1071 1042-7163
Popis:	Reactions of different electrophiles (alkyl halides, aldehydes, N-sulfinylimines, imines, etc) with (S)-2-p-toluenesulfinyl toluene and their alkyl, triisopropylsilyloxy, and methylthio derivatives at benzylic position, in the presence of LDA, allow the synthesis of a variety of enantiomerically pure benzylic centers, whose configuration is efficiently controlled by the γ-sulfinyl group, according to 1,4-asymmetric induction processes. With prochiral electrophiles, the 1,5-asymmetric induction processes can also be controlled either by modifying their steric or electronic features or by incorporating an additional chiral center at the electrophiles. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:537–548, 2007; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20342
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::11eca047bbd075235b9a5bd60b668dc7 https://doi.org/10.1002/hc.20342 Zobrazit plný text záznamu