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Org Lett. 2007 Oct 11;9(21):4151-4. Epub 2007 Sep 15.

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

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  • 1The State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 200032 Shanghai, China.


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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