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oai:mountainscholar.org:10217/2358392025-12-30T03:35:56Zcom_10217_100532com_10217_100000com_10217_100367com_10217_100303col_10217_100536col_10217_100368

Sinclair, Peter John, author Williams, Robert M., advisor 2022-11-28T17:44:52Z 2022-11-28T17:44:52Z 1987 https://hdl.handle.net/10217/235839 https://doi.org/10.25675/3.024707 A new asymmetric synthesis of α-monosubstituted-α-amino acids using D- and L-erythro-4-benzy loxycarbonyl-5,6-diphenyl-2,3,5,6-tetrahydro-1,4-oxazin-2-ones 108 as amino acid templates is described. Bromination of 108 with NBS generates the key electrophilic glycinate 132 which couples with a variety of carbon nucleophiles with high diastereoselectivity to afford the amino acid precursors 134. Catalytic hydrogenation of homologated heterocycles 134 directly furnishes the zwitterionic α-amino acids in high enantiomeric excess. Dissolving metal reduction of 134 permits the preparation of unsaturated amino acids while use of erythro-4-t-butoxycarbonyl-5,6-diphenyl-2,3,5,6-tetrahydro-1,4-oxazin-2-one 160 allows the direct preparation of t-BOC protected α-amino acids. The synthetic approaches to a number of biologically interesting amino acids are described and mechanistic aspects of the coupling reaction are discussed. doctoral dissertations English eng Colorado State University. Libraries Catalog record number (MMS ID): 991010249629703361 QD431.S67 1987 1980-1999 Copyright and other restrictions may apply. User is responsible for compliance with all applicable laws. For information about copyright law, please see https://libguides.colostate.edu/copyright. Amino acids -- Synthesis The asymmetric synthesis of amino acids via electrophilic glycinates Text Doctor of Philosophy (Ph.D.) Doctoral Chemistry Colorado State University This Item is protected by copyright and/or related rights (https://rightsstatements.org/vocab/InC/1.0/). You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s). open.access