Asymmetric synthesis of .alpha.-cycloalkylalkyl substituted meth

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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564336, C07D21302, C07C21101

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058564977

ABSTRACT:
This invention relates to process for asymmetrically producing enantiomerically pure .alpha.-cycloalkylalkyl substitututed methanamines from .alpha.-pinene. One key step of the process of this invention utilizes the oxidation product of .alpha.-pinene, hydroxy pinanone, as a chiral auxiliary to direct the stereoselective alkylation of the corresponding ketimine. This invention also relates to key intermediates useful in the processes referred to herein.

REFERENCES:
patent: 4595531 (1986-06-01), Milkowski et al.
patent: 4598093 (1986-07-01), Tahara et al.
patent: 5169971 (1992-12-01), Inomata et al.
patent: 5296486 (1994-03-01), Lazer et al.
March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 1992, 4th edition, Wiley & Sons, Inc., pp. 822-825 and 1168.
Mancuso, A.J. et al, Synthesis, 1981, pp. 165-185.
Morrison, R.T. et al, Organic Chemistry, 4th edition, 1983, Allyn & Bacon, Inc., p. 250.
Chen, Y. et al, Synth. Comm. 1989, 19(7-8), pp. 1423-1430, online results only.
Chen, Y. et al, Huaxue Xuebao, 1990, 48(11), pp. 1131-1135, online results only.
Lazer, E.S. et al, J. Med. Chem. 1994, 37, pp. 913-923.
Aiqiao, M. et al, Synth. Comm. 1991, 21(22), pp. 2207-2212.
Carlson, R.G. et al, J. Org. Chem. 1971, 36(16), pp. 2319-2324.
Jefford, C.S. et al, Tetrahedron Lett. 1994, 35(34), pp. 6275-6278.
Chen, Y. et al, Synth. Commun. 1989, 19(7-8), pp. 1423-1430.
European Search Report for Appl. No. EP 96 11 9658, (May 2, 1997).
Erdik, E. and Matteson, D.S., "Kinetics of Osmium Tetraoxide Catalyzed Trimethylamine N-Oxide Oxidations of Cyclohexene and .alpha.-Pinene to Diols," J. Org. Chem., 54:2742-2748 (1989).
Ray, R. and Matteson, D.S., "Osmium Tetroxide Catalyzed Hydroxylation of Hindered Olefins," Tetrahedron Letters 21:449-450 (1980).
Aiqiao, M. et al., "Asymmetric Synthesis XV: Enantioselective Syntheses of (R) or (S)-.alpha.-substituted-(2-Pyridyl) Methylamines Via Chiral Pinanone Ketimine Template," Synthetic Communications 21(21):2207-2212 (1991).
Dondoni, A. et al., "Alkylation of Camphor and Pinanone Imines of 2-(Aminomethyl)thiazole. Enantioselective Synthesis of 2-(1-Aminoalkyl)thiazoles," Synthesis 5:641-646 (May 1996).
Miao, C. et al., "A Simple and Effective Enantiomeric Synthesis Of A Chiral Primary Amine," Tetrahedron Letters 34(14):2259-2262 (1993).
Yuanwei, C. et al., "Asymmetric Synthesis VIII: Enantioselective Synthesis of (R) or (S)-.alpha.-Subsituted Benzylamines Via Chiral Pinanone Ketimine Template," Synthetic Communications 19(7/8):1423-1430 (1989).
Yuanwei, C. et al., "Asymmetric synthesis of optically active-.alpha.-substituted benzylamines," Chem. Abstracts 114(1): 592, Abstract No. 6009d (1991).
Ray, R. and Matteson, D.S., "A Highly Efficient Osmium Tetroxide Catalyzed Oxidation of Sterically hindered Olefins to Diols," J. Indian Chem. Soc. 59(2):119-23 (Feb. 1982).
VanRheenen, V. et al., "An Improved Catalytic Os04 Oxidation of Olefins to Cis-1,2-glycols Using Tertiary Amine Oxides as the Oxidant," Tetrahedron Letters, 23:1973-1976 (1976).

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