Palladium-catalyzed intramolecular asymmetric hydroamination, hydroalkoxylation, and hydrocarbonation of alkynes

Nitin T. Patil, Léopold Mpaka Lutete, Huanyou Wu, Nirmal K. Pahadi, Ilya D. Gridnev, Yoshinori Yamamoto

Research output: Contribution to journalArticlepeer-review

126 Citations (Scopus)

Abstract

A conceptually novel approach for asymmetric intramolecular hydroamination, hydroalkoxylation and hydrocarbonation of alkynes using chiral palladium catalysts are described. The reactions of the aminoalkynes 5, alkynols 7, and alkynylmethines 9 in the presence of Pd2(dba)3·CHCl 3/PhCOOH/renorphos 4 in benzene (or benzene-hexane) at 100 °C gave the corresponding cyclization products (nitrogen heterocycles 6, oxygen heterocycles 8, and carbocycles 10) in good yields with good enantioselectivities. The origins of enantioselectivities in the hydroamination reaction are discussed based on DFT computations.

Original languageEnglish
Pages (from-to)4270-4279
Number of pages10
JournalJournal of Organic Chemistry
Volume71
Issue number11
DOIs
Publication statusPublished - 2006 May 26

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Palladium-catalyzed intramolecular asymmetric hydroamination, hydroalkoxylation, and hydrocarbonation of alkynes'. Together they form a unique fingerprint.

Cite this