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‘meso-Selective’ functionalisation of N-benzyl-α-methylbenzylamine derivatives by α-lithiation and alkylation

✍ Scribed by Ryan A Bragg; Jonathan Clayden; Christel J Menet

Book ID
104250579
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
105 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

Lithiation and methylation of amide and carbamate derivatives of a-methylbenzylamine proceeds with high diastereoselectivity in favour of meso bis-a-methylbenzylamine derivatives. Carboxylation of the intermediate organolithium is also diastereoselective, and with N-Boc p-methoxy-a-methylbenzylamine as starting material, oxidative cleavage provides a new asymmetric route to phenylglycine. Other electrophiles give a range of stereochemical outcomes, apparently depending on the stereospecificity of their reactions with a pair of diastereoisomeric organolithiums of low to moderate configurational stability.

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Preparation of 1,2- and 1,4-diols via selective cleavage of C-benzotriazole bonds in reductive lithiations of N-(α-alkoxy-benzyl- and -allyl-)benzotriazoles
✍ Alan R. katritzky; Weiliang Bao; Ming Qi; Clara N. Fali; Indra Prakash 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 170 KB

Selective cleavage of C-benzotriazole bonds in the presence of C-O bonds is reported for the reductive lithiation of N-(ct-alkoxybenzyl)benzotriazoles and N-(a-alkoxyallyl)benzotriazoles in a onestep or two-step process. Trapping of the intermediates with carbonyl compounds gave unsymmetrically prot