Enantioselective syntheses of α-methylene butyrolactones via asymmetric aminocarbonylation of tungsten–prop-2-ynyl compounds

Abstract

A tungsten–η¹-vinylprop-2-ynyl compound undergoes enantioselective aminocarbonylation to afford an optically pure tungsten–π-γ-lactone; this π-allyl complex is useful for the efficient synthesis of optically pure α-methylene butyrolactone.

References

1. Advances in Metal–Organic Chemistry, ed. L. S. Liebeskind, JAI Press Inc., Greenwich, CT, 1989–1996, vol. 1–5.
2. S. G. Davies, Aldrichim. Acta, 1990, 31.
3. L. S. Hegedus, Transition Metals in the Synthesis of Complex Organic Molecules, University Science Books, Mill Valley, CA, 1994, ch. 4, p. 103.
4. A. J. Pearson, Synlett, 1990, 10.
5. A. J. Pearson, in Comprehensive Organometallic Chemistry, ed. G Wilkinson, F. G. A. Stone and E. W. Abel, Pergamon, Oxford, 1995, vol. 12, p. 637.
6. (a) W.-J. Vong, S.-M. Peng, S.-H. Lin, W.-J. Lin and R.-S. Liu, J. Am. Chem. Soc., 1991, 113, 573; (b) C.-C. Chen, J.-S. Fan, S.-J. Shieh, G.-H. Lee, S.-M. Peng, S.-L. Wang and R.-S. Liu, J. Am. Chem. Soc., 1996, 118, 9279.
7. D. A. Evans, F. Urpi, T. C. Somers, J. S. Clark and M. T. Bilodeau, J. Am. Chem. Soc., 1990, 112, 8215.
8. M.-H. Cheng, Y.-H. Ho, G.-H. Lee, S.-M. Peng, S.-Y. Chu and R.-S. Liu., Organometallics, 1994, 13, 4082.
9. J. W. Faller and D. L. Linebarrier, J. Am. Chem. Soc., 1989, 111, 1939; J. W. Faller, J. A. John and M. R. Mazzier, Tetrahedron Lett., 1989, 31, 1769.