Categories: C-C Bond Formation > Cyclic compounds > Cyclic alcohols

Synthesis of cyclohexanols

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Recent Literature

A tandem 1,4-reduction-aldol cyclization is induced by exposure of monoenone monoketones to catecholborane in THF at ambient temperature. Six-membered cyclic aldol products are formed in excellent yield with high levels of syn diastereoselectivity for aromatic and heteroaromatic enones. Five-membered ring formation proceeds less readily, but the yield is improved through addition of Rh(I) salts.
R. R. Huddleston, D. F. Cauble, M. J. Krische, J. Org. Chem., 2003, 68, 11-14.

Treatment of β,β-disubstituted-α,β-unsaturated ketones bearing a ketone residue with in situ generated, catalytic CuH ligated by a nonracemic ligand leads to cyclic aldol products with three newly created adjacent chiral centers. Excellent diastereoselectivities and enantioselectivities are obtained for several examples studied.
B. H. Lipshutz, B. Amorelli, J. B. Unger, J. Am. Chem. Soc., 2008, 130, 14378-14379.

B. H. Lipshutz, B. Amorelli, J. B. Unger, J. Am. Chem. Soc., 2008, 130, 14378-14379.

An efficient lithium amide-induced intramolecular cyclopropanation of bishomoallylic and trishomoallylic epoxides is described. The methodology is used in an asymmetric synthesis of sabina ketone.
D. M. Hodgson, Y. K. Chung, J.-M. Paris, J. Am. Chem. Soc., 2004, 126, 8654-8655.