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. 2007 Oct 11;9(21):4151-4.
doi: 10.1021/ol701669b. Epub 2007 Sep 15.

Enantioselective formal [3+3] annulation for the direct construction of bicyclic skeletons with four stereogenic centers

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Enantioselective formal [3+3] annulation for the direct construction of bicyclic skeletons with four stereogenic centers

Chun-Li Cao et al. Org Lett. .

Abstract

An enantioselective formal [3+3] annulation reaction of cyclic ketones with enones has been developed. In the presence of 20 mol % of pyrrolidine-thiourea 1a or N-(pyrrolidin-2-ylmethyl)trifluoromethanesulfonamide 1i, the reactions afford bicyclo [3.3.1] adducts in moderate to good yields with good to high enantioselectivities under mild conditions.

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