Stereospecific synthesis of aldols

Details Stereospecific synthesis of aldols Stereospecific synthesis of aldols

1993-11-24

1995-06-20

Shaver, Paul F.

Organic compounds -- part of the class 532-570 series

Organic compounds

Silicon containing

568309, 568322, 568403, 568405, 568406, 568811, 568853, C07F 708, C07F 718

Patent

active

054262062

ABSTRACT:
Methods are provided for preparing all four diastereomers of 2-alkyl-3-hydroxyalkanals, 2-alkyl-3-silyloxyalkanals, and the like, with high enantiocontrol, using non-aldol chemistry. The synthetic methods also provide novel, stereospecific routes to polypropinates and chiral 2-substituted-1,3 diols.

REFERENCES:
patent: 5037855 (1991-08-01), Sato
patent: 5329023 (1994-07-01), Brussee et al.
S. Masamune et al., Aldrichimica Acta, Advances in Stereochemical Control: The 1,2-and 1,3-Diol Systems.sup.1, Aldrich Chemical Co., vol. 15, No. 3, (1982), pp. 47-68.
A. Togni et al., Cooperativity of Chirality in Homogeneous Catalysis: The Gold(I)-Catalyzed Aldol Reaction and the Vanadium(IV)-Catalyzed Hetero Diels-Alder Cycloaddition, Chirality, vol. 3, No. 4, (1991) pp. 331-340.
Manfred Braun, Recent Developments in Stereoselective Aldol Reactions, Advances in Carbanion Chemistry, JAI Press, Inc., vol. 1, (1992) pp. 177-247.
Heathcock, C. H. "The Aldol Addition Reaction," in Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York 1984; vol. 3, Ch. 2 pp. 111-115.
Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem 1982, 13, 1-6.
Paterson, I.; Lister, M. A.; McClure, C. K. Tetrahedron Lett 1986, 27, 4787-4790.
Reetz, M. T.; Kunisch, F.; Heitman, P. Tetrahedron Lett. 1986, 27, 4721-2724.
Maruoka, K.; Sato, J.; Yamamoto, H. Tetrahedron 1992, 48, 3749-3762.
Maruoka, K.; Ooi, T.; Yamamoto, H., J. Am. Chem. Soc. 1989, 111 6431-6998.
Maruoka, K.; Ooi, T.; Nagahara, S.; Yamamoto, H. Tetrahedron 1991, 47, 6983-6998.
Maruoka, K.; Hagesawa, M.; Yamamoto, H.; Suzuki, K.; Shimazaki, M.; Tsuchihashi, G. J. Am Chem. Soc. 1986, 108, 3827-3829.
Suzuki, K.; Miyazawa, M.; Tsuchihashi, G. Tetrahedron Lett. 1987, 28, 3515-3518.
Shimazaki, M.; Hara, H.; Suzuki, K.; Tsuchiahashi, G. Tetrahedron Lett. 1987, 28, 5891-5894.
Still, W. C.; Gennari, C. Tetrahedron Lett 1983 24, 4405-4408.
Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem Rev., 1993, 93, 1307-1370.
Hanson, R. M.; Sharpless, K. B., J. Org. Chem 1986, 51, 1922-1525.
Olah, G. A.; Farooq, I.; Farnia, S. M. F.; Olah, J. A., J. Am Chem Soc. 1988, 110, 2560-2565.
Alexakis, A.; Mutti, S.; Normant, J. F.; Mangency, P. Tetrahedron Asymm. 1990, 1, 437-440.
Basavaiah, D.; Sarma, P. K. S. J Chem Soc., Chem. Commun 1992, 955-557.
Sreekumar, C.; Darst, K. P.; Still, W. S. J. Org. Chem 1980, 45, 4260-4262.
Davis, A. P.; Jaspars, M. Angew. Chem. Int. Ed. Engl., 1992, 31, 470-471.

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