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1,2‐Bond shift of the Fe(CO) 3 moiety in the 1,5‐ O ‐heterocyclization of (1,3‐dienyl)‐tricarbonyliron diols: Application to the synthesis of novel phosphocholines
Author(s) -
Braun Alain,
Lellouche JeanPaul Moshe
Publication year - 2002
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1560/wgvk-au3q-5vjv-rexd
Subject(s) - chemistry , moiety , cationic polymerization , intramolecular force , stereoselectivity , stereochemistry , catalysis , optically active , medicinal chemistry , combinatorial chemistry , organic chemistry
A novel concept of intramolecular cationic 1,5‐ O ‐heterocyclization of ψ‐ exo ‐/ψ‐ endo ‐(1,3‐dienyl)tricarbonyliron diols has been demonstrated to occur under acid catalysis with a quite unusual 1,2‐migration of the complexation site. This cationic cyclization has been shown to be stereoselective when involving homochiral precursor diols. It allowed straightforward access to new racemic and optically active conformationally locked alkylphosphocholines as potential anticancer agents.