- An expeditious and efficient bromomethylation of thiols: Enabling bromomethyl sulfides as useful building blocks
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A facile and highly efficient method for the bromomethylation of thiols, using paraformaldehyde and HBr/AcOH, has been developed, which advantageously minimizes the generation of highly toxic byproducts. The preparation of 22 structurally diverse α-bromomethyl sulfides illustrates the chemo-tolerant applicability while bromo-lithium exchange and functionalization sequences, free radical reductions, and additions of the title compounds demonstrate their synthetic utility.
- Silva-Cuevas, Carolina,Paleo, Ehecatl,León-Rayo, David F.,Lujan-Montelongo, J. Armando
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p. 24654 - 24659
(2018/07/25)
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- Clean, high-yield preparation of S,S and R,S amino acid isosteres
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The present invention provides compounds and methods that can be used to convert the intermediate halomethyl ketones (HMKs), e.g., chloromethyl ketones, to the corresponding S,S- and R,S-diastereomers. More particularly, the present invention provides: (1) reduction methods; (2) inversion methods; and (3) methods involving the epoxidation of alkenes. Using the various methods of the present invention, the R,S-epoxide and the intermediary compounds can be prepared reliably, in high yields and in high purity.
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