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ALDOL COUPLINGS OF CHIRAL FRAGMENTS WITH KINETIC RESOLUTION: SCOPE AND LIMITATIONS

“The Thiopyran Route to Polypropionates” is a synthetic strategy that involves
the stepwise aldol reactions of 6 and 7a to rapidly access stereochemically complex
tetrapropionate 8 and hexapropionate synthons 72 or 73. Coupling racemic 7a with any
of the four enantioenriched diastereomers 8 with kinetic resolution (KR) is possible
with rational design of the reaction using the 'multiplicativity' rule. Thus, any of two of
the eight possible aldol adducts, 72 or 73, are selectively available from the same
reactants.

Identiferoai:union.ndltd.org:USASK/oai:ecommons.usask.ca:10388/ETD-2011-12-244
Date2011 December 1900
ContributorsWard, Dale
Source SetsUniversity of Saskatchewan Library
LanguageEnglish
Detected LanguageEnglish
Typetext, thesis

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