Starting from the 8-allyl substituted oxazolopiperidone lactam 2b, which is easily accessible from (R)-phenylglycinol and racemic δ-oxoester 1a, two-step sequences involving a stereoselective α-amidoalkylation reaction, either with inversion or retention of configuration, followed by a ring-closing metathesis, provide diastereodivergent routes to enantiopure cis- and trans-3,4,4a,5,8,8a-hexahydro-1H-quinolin-2-ones.
Stereocontrolled synthesis of enantiopure cis- and trans-3,4,4a,5,8,8a-hexahydro-1H-quinolin-2-ones / M. Amat, M. Perez, A.T. Minaglia, D. Passarella, J. Bosch. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 19:20(2008), pp. 2406-2410. [10.1016/j.tetasy.2008.10.007]
Stereocontrolled synthesis of enantiopure cis- and trans-3,4,4a,5,8,8a-hexahydro-1H-quinolin-2-ones
D. PassarellaPenultimo
;
2008
Abstract
Starting from the 8-allyl substituted oxazolopiperidone lactam 2b, which is easily accessible from (R)-phenylglycinol and racemic δ-oxoester 1a, two-step sequences involving a stereoselective α-amidoalkylation reaction, either with inversion or retention of configuration, followed by a ring-closing metathesis, provide diastereodivergent routes to enantiopure cis- and trans-3,4,4a,5,8,8a-hexahydro-1H-quinolin-2-ones.
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