Diastereoselectivity in nucleophilic displacement reactions at phosphorus; isolation and characterization of a pentacoordinated intermediate

Autor:	Peter Rüedi, Franco Alberto Merckling
Rok vydání:	1996
Předmět:	chemistry.chemical_classification Displacement reactions chemistry Base (chemistry) Nucleophile Stereochemistry Phosphorus Organic Chemistry Drug Discovery chemistry.chemical_element Reaction intermediate Biochemistry
Zdroj:	Tetrahedron Letters. 37:2217-2220
ISSN:	0040-4039
DOI:	10.1016/0040-4039(96)00275-4
Popis:	Reaction of the axially substituted trans -3-chloro-2,4-dioxa-3λ 5 -phosphabicyclo[4.4.0]decan-3-one ((±)- 1 ) with O- and S-nucleophiles in the presence of DBN preferentially proceeds with retention at P, whereas the epimeric ration is reversed with DBU as the auxiliary base. N-nucleophiles exclusively react with inversion; in the presence of DBN, a pentacoordinated compound ( 5 ), which is considered to be a reaction intermediate, was isolated as the main product.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::7d9f6f927719ccd9e71b693cfe3aa146 https://doi.org/10.1016/0040-4039(96)00275-4 Zobrazit plný text záznamu Full Text from ScienceDirect