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Synlett 1998; 1998(8): 810-816
DOI: 10.1055/s-1998-1784
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Stereocontrol with Rotationally Restricted Amides

Jonathan Clayden*
  • *Department of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK; E-mail: j.p.clayden@man.ac.uk
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Publication History

Publication Date:
31 December 2000 (online)

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Rotational restriction in amides can be a blessing or a curse: this Account sets out highlight the former, in the light of our discovery that rotationally restricted amides have a remarkable ability to control stereochemistry. We start with an outline of the degree of steric hindrance to amide rotation required for a rotationally restricted amide group can give rise to stereoisomers, and move on to ways of using the amide group to control new stereogenic centres and to report the stereochemical details of substitution reactions. Amide stereochemistry can also respond to stereogenic centres within a molecule through "conformational interlocking", and we finish with an overview of the current state of affairs with regard to the use of amides to relay stereochemical information to remote stereogenic centres.

amide - lithiation - stereochemistry - atropisomers - conformation