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Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)‐2‐ epi ‐Hyacinthacine A 2 and (–)‐3‐ epi ‐Hyacinthacine A 1
Author(s) -
Marjanovic Jasna,
Divjakovic Vladimir,
Matovic Radomir,
Ferjancic Zorana,
Saicic Radomir N.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300716
Subject(s) - aldol reaction , chemistry , diastereomer , aldehyde , reagent , asymmetric induction , total synthesis , enantioselective synthesis , organocatalysis , proline , stereochemistry , organic chemistry , catalysis , amino acid , biochemistry
The stereodivergent synthesis of two hyacinthacine analogues, which relies on an organocatalyzed aldol addition, is described. The aldol addition of dioxanone to an α‐ N ‐carbobenzyloxy‐substituted chiral aldehyde, promoted by both ( R )‐ and ( S )‐proline, proceeds in reasonable yields with acceptable diastereomeric ratios. The success of the reaction may be due to the use of an acyclic aldehyde acceptor, which allows reagent control of the stereochemical outcome of the key aldolization step in both the matched and mismatched cases.