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α-Aminated methyllithium by DTBB-catalysed lithiation of a N-(chloromethyl) carbamate by Javier Ortiz; Albert Guijarro; Miguel Yus is a Chemistry article available to read on EtoBox.

What is α-Aminated methyllithium by DTBB-catalysed lithiation of a N-(chloromethyl) carbamate about?

The reaction of O-tert-butyl-N-(chloromethyl)-N-methyl carbamate (1) with lithium powder and a catalytic amount of 4,4'-di-tert-butylbiphenyl (DTBB, 2.5 mol %) in the presence of different electrophiles [Me3SiC1, iBuCHO, tBuCHO, PhCHO, 4-MeOC6HaCHO, (CH2)4CO, MeCOnpr, Et2CO, MeCO(CH2)2CH=CH2, PhCOMe, PhCOnBu, Ph2CO] in THF at -78°(2 leads, after hydrolysis with water, to the expected functionalised carbamates 2. Carbamates 2 derived from carbonyl compounds are deprotected with hydrogen chloride (for aromatic aldehyde or ketone derivatives) or with a mixture of phenol and trimethylsilyl chloride (for aliphatic aldehyde derivatives) giving substituted 1,2-diols 4.

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Author

Javier Ortiz; Albert Guijarro; Miguel Yus

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

1999

Language

EN

Field

Chemistry (Physical Sciences)