Pauson-Khand Reaction

I. U. Khand et al., J. Chem. Soc. Perkin Trans. I 1973, 977.

The formal [2+2+1] cycloaddition of an alkene, alkyne, and carbon monoxide to form cyclopentenones:

Use of a chiral auxillary: X. Verdaguer et al., J. Am. Chem. Soc. 116, 2153 (1994); V. Bernardes et al., J. Org. Chem. 60, 6670 (1995); J. Adrio, J. C. Carretero, J. Am. Chem. Soc. 121, 7411 (1999). Catalytic version: N. Jeong et al., ibid. 116, 3159 (1994). Intramolecular cyclizations: Y.-T. Shiu et al., ibid. 121, 4066 (1999); F. A. Hicks et al., ibid. 5881; P. M. Breczinski et al., Tetrahedron 55, 6797 (1999). Reviews: N. E. Schore, Org. React. 40, 1-90 (1991); idem, Comp. Org. Syn. 5, 1037-1064 (1991); S. T. Ingate, J. Marco-Contelles, Org. Prep. Proced. Int. 30, 123-143 (1998); O. Geis, H.-G. Schmalz, Angew. Chem. Int. Ed. 37, 911-914 (1998).