4.8 Article

Highly Diastereoselective Synthesis of Tetrahydropyridines by a C-H Activation-Cyclization-Reduction Cascade

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 9, Pages 4064-4067

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja2119833

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Funding

  1. NIH [GM069559]
  2. Office of Energy Research, Office of Basic Energy Sciences, Chemical Sciences Division, U.S. Department of Energy [DE-AC02-05CH11231]
  3. Swiss National Science Foundation [PBZHP2-130-966]

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A versatile reaction cascade leading to highly substituted 1,2,3,6-tetrahydropyridines has been developed. It comprises rhodium(I)-catalyzed C-H activation alkyne coupling followed by electrocyclization and subsequent acid/borohydride-promoted reduction. This one-pot procedure affords the target compounds in up to 95% yield with >95% diastereomeric purity.

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