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Enantiomerically Enriched Α-Methyl Amino Acids. Use Of An Acyclic, Chiral Alanine-Derived Dianion With A High Diastereofacial Bias., David B. Berkowitz, Marianne K. Smith
Enantiomerically Enriched Α-Methyl Amino Acids. Use Of An Acyclic, Chiral Alanine-Derived Dianion With A High Diastereofacial Bias., David B. Berkowitz, Marianne K. Smith
David Berkowitz Publications
Hindered esters derived from N-benzoylalanine and the following chiral alcohols have been synthesized: (1) (−)-isopinocampheol; (2) (−)-trans-2-phenylcyclohexanol and (3) (−)-8-phenylmenthol. Sequential treatment of these esters with LDA (1.2 equiv.) and n-butyllithium (2.4 equiv.) at −78°C in THF generates the corresponding chiral dianions. Alkylation of each of these with benzyl bromide reveals that only the (−)-8-phenylmenthyl auxiliary confers a high diastereofacial bias upon its derivative dianion. In fact, that dianion (6) consistently displays diastereomeric ratios in the range of 89:11 to 94:6 for alkylations with a spectrum of nine alkyl halides. If one recrystallization step is …
Free Α-Oxiranyl Amino Acids, David B. Berkowitz, Michelle L. Pedersen
Free Α-Oxiranyl Amino Acids, David B. Berkowitz, Michelle L. Pedersen
David Berkowitz Publications
Analogues of natural amino acids, in which the α-proton is replaced by an unsubstituted epoxide ring, are potential mechanism-based inhibitors for pyridoxal phosphate dependent enzymes.1 Yet, free α-oxiranyl amino acids have remained elusive until now. The synthesis of an α-(phenyl-substituted)oxiranyl amino ester has been reported. However, the accessibility and stability of the corresponding free, zwitterionic α-oxiranyl amino acid remained an open question.9