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A Short Enantioselective Synthesis of Carbanucleosides
Author(s) -
Trost Barry M.,
Madsen Robert,
Guile Simon G.,
Elia Andrew E. H.
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199615691
Subject(s) - desymmetrization , enantioselective synthesis , nucleophile , alkylation , stereochemistry , chemistry , tsuji–trost reaction , ligand (biochemistry) , catalysis , combinatorial chemistry , organic chemistry , biochemistry , receptor
Surprisingly, purines , unlike other nucleophiles, affect the enantioselectivity of the Pd‐catalyzed desymmetrization of cis ‐3,5‐diacyloxycyclopent‐1‐enes 1 , even though they are formally not involved in the enantiodiscriminating step. Under suitable conditions this influence can be minimized. From 2 , the alkylated adenine and analogues 3 can be obtained, and the latter can be employed in the short asymmetric syntheses of antiviral agents (–)‐carbovir and (–)‐aristeromycin. X PhCO 2 ; Y OCONPh 2 , NH 2 , Cl; Z H, NH 2 , NHAc; L * chiral ligand.
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