Temperature-Dependent Direct Enantioconvergent Silylation of a Racemic Cyclic Allylic Phosphate by Copper(I)-Catalyzed Allylic Substitution

Autor:	Lukas B. Delvos, Martin Oestreich
Rok vydání:	2015
Předmět:	Allylic rearrangement chemistry.chemical_compound Silylation Nucleophile Chemistry Organic Chemistry Organic chemistry SN2 reaction Enantiomer Selectivity Silane Catalysis
Zdroj:	Synthesis. 47:924-933
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0034-1380157
Popis:	The near-quantitative transformation of a racemic cyclic allylic phosphate to a highly enantiomerically enriched allylic silane by allylic substitution with a silicon nucleophile is reported. The reaction is catalyzed by a chiral NHC–copper(I) complex. Experimental analysis revealed a rare case of a direct enantioconvergent transformation where the enantiomeric allylic phosphates converge to the same allylic silane by two distinctive SN2′ pathways with opposite diastereofacial selectivity.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::4c66f7ebf6c7dfc84b9e24c596c5aca4 https://doi.org/10.1055/s-0034-1380157 Zobrazit plný text záznamu