The development and application of enantioselective reactions of masked acyl cyanide reagents /

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Bibliographic Details
Author / Creator:	Yang, Kin, author.
Imprint:	2015. Ann Arbor : ProQuest Dissertations & Theses, 2015
Description:	1 electronic resource (384 pages)
Language:	English
Format:	E-Resource Dissertations
Local Note:	School code: 0330
URL for this record:	http://pi.lib.uchicago.edu/1001/cat/bib/10773203

Hidden Bibliographic Details
Other authors / contributors:	University of Chicago. degree granting institution.
ISBN:	9781321985061
Notes:	Advisors: Viresh H. Rawal Committee members: Sergey A. Kozmin; Jared C. Lewis. This item must not be sold to any third party vendors. Dissertation Abstracts International, Volume: 76-12(E), Section: B. English
Summary:	Masked acyl cyanide (MAC) reagents are shown to be effective umpolung synthons for enantioselective additions to electrophiles. The reactions are catalyzed by chiral bifunctional catalysts and afford adducts in high yields and with excellent enantioselectivities. The addition products are unmasked to produce dicyanohydrins that, upon treatment with a variety of nucleophiles, provides access to ?-ketocarboxylic acid derivatives or ?-amino acid derivatives. The use of this umpolung synthon has enabled, in enantiomerically enriched form, the first total synthesis of the prenylated phenol (+)-fornicin C. Notably, the methodology also provides an alternative method for peptide bond formation.

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