Asymmetric Synthesis of Monosubstituted and α,α-Disubstituted α-Amino Acids via Diastereoselective Glycine Enolate Alkylations

Journal of the American Chemical Society

Volumn 113, Issue 24, 1991, Pages 9276-9286

  Williams, Robert M ^a   Im, Myeong Nyeo ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE;

ARTICLE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0026326741     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00024a038     Document Type: Article

References (58)

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56. The use of the protected “long cysteine” in peptide synthesis was examined in Professor Peter G. Schultz's laboratory at Berkeley. Compound 18 was incorporated into several small peptides by standard carbodiimide coupling chemistry. Unfortunately, all attempts to cleave the p-methoxybenzyl group to release the free sulfhydryl (HF, DDQ, TFA, etc) resulted in cleavage of the nonbenzylic C-S bond. Prof. Schultz is acknowledged for suggesting the synthesis of this amino acid and for helpful discussions.
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