Highly diastereoselective synthesis of β-hydroxy carbonyl compounds using π-allyltricarbonyliron lactone complexes: a formal 1,7-asymmetric induction of chirality in a Mukaiyama aldol reaction
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Steven V. Ley
Abstract
The reaction of π-allyltricarbonyliron lactone complex 2 with a variety of achiral aldehydes affords the corresponding aldol products in good yields and with good to excellent levels of stereocontrol.
References
For general reviews on the aldol reaction:
C. H. Heathcock,
B. Moon. Kim,
S. F. Williams,
S. Masamune,
I. Paterson and
C. Gennari, in
Comprehensive Organic Synthesis, ed.
B. M. Trost and I. Fleming,
Pergamon,
Oxford,
1991, vol. 2 and references cited therein Search PubMed; A. S. Franklin and I. Paterson, Contemp. Org. Synth., 1994, 1, 317 Search PubMed and references cited therein.
For approaches to the asymmetric synthesis of α-unsubstituted β-hydroxy ketones: M. Braun, Angew. Chem., Int. Ed. Engl., 1987, 26, 24 Search PubMed; M. Braun, in
Advances in Carbanion Chemistry, ed.
V. Snieckus,
JAI,
Greenwich,
1992,
p. 216 CrossRef; M. Franck-Neumann, P.-J. Colson, P. Geoffroy and K. M. Taba, Tetrahedron Lett., 1992, 33, 1903 CrossRef; M. Franck-Neumann, P. Bissinger and P. Geoffroy, Tetrahedron Lett., 1997, 38, 4469 Search PubMed; 1997,
38,
4473 CrossRefCAS; 1997,
38,
4477 CrossRefCAS; M. Sodeoka, R. Tokunoh, F. Miyazaki, E. Hagiwara and M. Shibasaki, Synlett, 1997, 463 CrossRefCAS; K. Mikami, S. Matsukawa, M. Nagashima, H. Funabashi and H. Morishima, Tetrahedron Lett., 1997, 38, 579 CrossRefCAS; Y.-M. Li, X.-J. Yao, X. Feng, X.-M. Wang and J.-T. Wang, J. Organomet. Chem., 1996, 509, 221 Search PubMed; E. M. Carreira, W. Lee and R. A. Singer, J. Am. Chem. Soc., 1995, 117, 3649 Search PubMed; K. Ishihara, T. Maruyama, M. Mouri, Q. Gao, K. Faruta and H. Yamamoto, Bull. Chem. Soc. Jpn., 1993, 66, 3483 CAS; E. J. Corey, C. L. Cywin and T. D. Roper, Tetrahedron Lett., 1992, 33, 6907 CrossRef; I. Paterson and J. M. Goodman, Tetrahedron Lett., 1989, 30, 997 CrossRefCAS; M. Muraoka, H. Kawasaki and K. Koga, Tetrahedron Lett., 1988, 29, 337 CrossRefCAS; M. T. Reetz, F. Kunisch and P. Heitmann, Tetrahedron Lett., 1986, 27, 4721 CAS.
For a general review on the Mukaiyama reaction: T. Mukaiyama, Org. React., 1982, 28, 203 Search PubMed.
For other examples of 1,7-asymmetric induction in organic synthesis: J. S. Carey and E. J. Thomas, J. Chem. Soc., Chem. Commun., 1994, 283 Search PubMed; G. A. Molander and K. L. Bobbitt, J. Am. Chem. Soc., 1993, 115, 7517 RSC.
Examples of remote asymmetric induction in aldol reactions of methyl ketones. 1,4-Asymmetric induction: B. R. Lagu and D. C. Liotta, Tetrahedron Lett., 1994, 35, 4485 Search PubMed; B. R. Lagu, H. M. Crane and D. C. Liotta, J. Org. Chem., 1993, 58, 4191 CrossRefCAS; B. M. Trost and H. Urabe, J. Org. Chem., 1990, 55, 3982 CrossRefCAS; I. Paterson, J. M. Goodman and M. Isaka, Tetrahedron Lett., 1989, 30, 7121 CrossRefCAS 1,5-Asymmetric induction: D. A. Evans, P. J. Coleman and B. Côté, J. Org. Chem., 1997, 62, 788 CrossRefCAS; I. Paterson, K. Gibson and R. M. Oballa, Tetrahedron Lett., 1996, 37, 8585 Search PubMed.
S. V. Ley, G. Meek, K.-H. Metten and C. Piqué, J. Chem. Soc., Chem. Commun., 1994, 1931 RSC; S. V. Ley, L. R. Cox, G. Meek, K.-H. Metten, C. Piqué and J. M. Worrall, J. Chem. Soc., Perkin Trans. 1, 1997, 3299 RSC.
S. V. Ley and L. R. Cox, Chem. Commun., 1996, 657 RSC; J. Chem. Soc., Perkin Trans. 1,
1997,
3315 Search PubMed.
D. A. Evans, D. L. Reiger and J. R. Cage, Tetrahedron Lett., 1990, 31, 7099 CrossRefCAS.
S. D. Rychnovsky and D. J. Skalitzky, Tetrahedron Lett., 1990, 31, 945 CrossRefCAS; S. D. Rychnovsky, B. Rogers and G. Yang, J. Org. Chem., 1993, 58, 3511 CrossRef.
For a general review on the synthetic utility of π-allyltricarbonyliron lactone complexes: S. V. Ley, L. R. Cox and G. Meek, Chem. Rev., 1996, 96, 423 Search PubMed and references cited therein.
S. V. Ley, S. Burckhardt, L. R. Cox and J. M. Worrall, Chem. Commun., 1997, 229 RSC.
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