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Title: Diastereoselective oxy-Michael addition of a new chiral water equivalent to electron deficient alkenes : synthesis of 1,2-amino alcohols and b-hydroxy malonates
Author: Buchanan, D. J.
Awarding Body: University of Cambridge
Current Institution: University of Cambridge
Date of Award: 2005
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Chapters 1 and 2: An introduction to the intermolecular oxy-Michael reaction and a brief overview of the methods used to synthesise 1,2-amino alcohols. Chapter 3: An oxy-Michael reaction was developed whereby the addition of (S)-6-methyltetrahydropyran into a,b-unsaturated monosubstituted nitro compounds allowed rapid access to synthetically important 1,2-amino alcohols. Chapter 4: A logical advancement of the oxy-Michael addition was the addition into a,b-unsaturated disubstituted nitro compounds. These molecules were also converted into the corresponding 1,2-amino alcohols. In addition sequential treatment of the oxy-Michael adduct with TPAP yielded the corresponding b-hydroxy ketone motif. Chapters 5 and 6: The highly stereoselective total syntheses of (R)-pronethalol and (R)-salmeterol were achieved using the new oxy-Michael method as the key step. Chapter 7: An expansion of the methodology to incorporate other conjugate acceptors was considered important. However, analogous d-lactol oxy-Michael additions into crotonate ester and pentenolide were unsuccessful. However, successful oxy-Michael addition into symmetrical a,b-unsaturated malonate systems yielded THP* protected b-hydroxy malonates. It is believed that such motifs shall be capable of transformation into b-hydroxy esters after further development.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available