TOWARD NEUROACTIVE PYRROLIDINES AND SYNTHETIC EFFICIENCY: DEVELOPMENT OF AN ASYMMETRIC AZA-MICHAEL ALDOL-LACTONIZATION ORGANOCASCADE PROCESS
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Date
2013-02-04
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Abstract
Described is the development an asymmetric aza-Michael aldol-lactonization organocascade process. This process enables the synthesis of highly-substituted pyrrolidines from α-amino ketones through an organocascade process. Boc-N-(L)-phenylalanine and Ts-N-(L)-alanine α-amino ketone substrates were synthesized by carrying out Weinreb ketone syntheses on their parent α-amino acid. The α-amino ketone substrates and acryloyl chloride were subjected to different aza-Michael aldol-lactonization conditions in order to test for the efficiency at which they react to form pyrrolidine products. The Ts-N-(L)-alanine α-amino ketone substrate, when reacted with homobenzootetramisole (± HBTM) as a nucleophile promoter and EtN(i-Pr)2 as stoichiometric base, showed the most promise in favoring the formation of pyrrolidine products.
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pyrrolidine, organocascade