Lewis acid mediated diastereoselective keto-ene cyclization on chiral perhydro-1,3-benzoxazines: synthesis of enantiopure cis-3,4-disubstituted 3-hydroxypyrrolidines |
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| Authors: | Celia Andrés Carlos D Rosón |
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| Institution: | Centro de Innovación en Química y Materiales Avanzados (CINQUIMA) and Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, Dr. Mergelina s/n, 47011 Valladolid, Spain |
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| Abstract: | Chiral 2-acyl-3-allyl-perhydro-1,3-benzoxazines derived from (−)-8-aminomenthol were easily cyclized in the presence of Lewis acids at 0 °C. The diastereoselectivity of the cyclization was dependent on the nature of the Lewis acid. The cyclization compounds can be transformed into enantiopure cis-3,4-disubstituted 3-hydroxypyrrolidines by ring opening of the N,O-acetal moiety and subsequent elimination of the menthol appendage. |
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| Keywords: | Carbonyl-ene cyclization Chiral 3-hydroxypyrrolidines Perhydro-1 3-benzoxazines Diastereoselective synthesis Lewis acids |
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