Journal
CHEMICAL SCIENCE
Volume 13, Issue 8, Pages 2355-2362Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1sc06259j
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Funding
- Science and Engineering Research Board, Department of Science and Technology, India [SPG/2020/000754, CRG/2018/000317]
- CSIR, India
- DST, India [DST/INSPIRE/04/2017/000446]
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A diastereoselective allylation of N-tert-butane sulfinyl alpha-iminoesters using allylboronic acids has been developed for obtaining optically active non-proteinogenic alpha-amino acid precursors with high yields and diastereoselectivities. This protocol offers gram-scale synthesis, broad functional group tolerance, excellent stereodivergence, post-synthetic modifications, and easy removal of the chiral auxiliary, making it applicable to various amino acids and short peptides for incorporation of these precursors at the N-terminal position.
A diastereoselective allylation of N-tert-butane sulfinyl alpha-iminoesters using allylboronic acids is developed to obtain optically active non-proteinogenic alpha-amino acid precursors in good yields and diastereoselectivities. Gram-scale synthesis, broad tolerance of functional groups, excellent stereodivergence, post-synthetic modifications, and easy removal of the chiral auxiliary are some of the key highlights. The protocol is applicable to various amino acids and short peptides, resulting in the incorporation of these precursors at the N-terminal position.
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