Asymmetric γ-Methoxyallylation with the Robust 10-TMS-9-Borabicyclo[3.3.2]decanes

Autor:	Lorell Muñoz-Hernández, John A. Soderquist
Rok vydání:	2009
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Aldimine chemistry Stereochemistry Reagent Organic Chemistry Side chain Physical and Theoretical Chemistry Selectivity Biochemistry Medicinal chemistry Derivative (chemistry)
Zdroj:	Organic Letters. 11:2571-2574
ISSN:	1523-7052 1523-7060
DOI:	10.1021/ol900865y
Popis:	The asymmetric gamma-methoxyallylboration of aldehydes with the configurationally very stable 1 gives nonracemic threo-beta-methoxyhomoallylic alcohols 7 (65-93%) with excellent selectivity (96-99% de, 98-99% ee). The corresponding homoallylic amines 10 are obtained from N-H aldimines with similar efficiency (72-96%) and with excellent diastereoselectivity (98% de) but with lower enantioselectivity (56-86% ee). These new reagents provide ready access to a Taxol side chain derivative.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::119ede1e8d9ad3dcf5bf2ee485524ce0 https://doi.org/10.1021/ol900865y Zobrazit plný text záznamu