Tetrahedron Letters p. 7735 - 7738 (1999)
Update date:2022-07-30
Topics:
Miranda, Paulo Cesar M. L.
Correia, Carlos Roque D.
The diastereofacial selectivity of enecarbamates bearing a chiral auxiliary was evaluated for the [2+2]cycloaddition with dichloroketenes. Diastereofacial selectivity ranged from zero (bornyl and menthyl) to 60% (Greene's auxiliary and 8-phenylmenthyl). Chromatography separation of the diastereomeric azacyclobutanones derived from the 8-phenylmenthyl enecarbamate permitted an enantiodivergent synthesis of the (-)-Geissman-Waiss lactone, a key intermediate in the synthesis of necine bases.
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Doi:10.1016/s0020-1693(99)00105-x
(1999)Doi:10.1002/(SICI)1099-1344(199909)42:9<835::AID-JLCR244>3.0.CO;2-R
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(1999)Doi:10.1016/j.jorganchem.2013.09.034
(2014)
