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Diastereoselective Addition of Terminal Alkynes to Chiral Nitrones: Asymmetric Synthesis of Propargylic N-Hydroxylamines.

✍ Scribed by Samir K. Patel; Sandrine Py; Shashi U. Pandya; Pierre Y. Chavant; Yannick Vallee


Book ID
101943161
Publisher
John Wiley and Sons
Year
2003
Weight
19 KB
Volume
34
Category
Article
ISSN
0931-7597

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Diastereoselective addition of terminal
✍ Samir K. Patel; Sandrine Py; Shashi U. Pandya; Pierre Y. Chavant; Yannick VallΓ©e πŸ“‚ Article πŸ“… 2003 πŸ› Elsevier Science 🌐 English βš– 521 KB

1,3-Asymmetric induction in the Et 2 Zn-catalyzed addition of terminal alkynes was studied with nitrones bearing a chiral auxiliary on their nitrogen atom. The obtained propargylic N-hydroxylamines were generally isolated in good yields and with satisfactory to excellent diastereoselectivities.

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An InBr 3 -catalyzed direct and efficient alkynylation of nitrones with terminal alkynes was developed. The process enables practical synthesis of a wide range of synthetically useful N-hydroxy-propargyl amine derivatives in good yields under mild conditions. The application of this method to optica