TY - JOUR
T1 - 1,2-Bond shift of the Fe(CO)3 moiety in the 1,5-O-heterocyclization of (1,3-dienyl)-tricarbonyliron diols
T2 - Application to the synthesis of novel phosphocholines
AU - Braun, Alain
AU - Lellouche, Jean Paul
PY - 2001
Y1 - 2001
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0039301832&partnerID=8YFLogxK
U2 - 10.1560/wgvk-au3q-5vjv-rexd
DO - 10.1560/wgvk-au3q-5vjv-rexd
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AN - SCOPUS:0039301832
SN - 0021-2148
VL - 41
SP - 329
EP - 338
JO - Israel Journal of Chemistry
JF - Israel Journal of Chemistry
IS - 4
ER -