The stereoselectivity of the conjugate addition of carbon nucleophiles to the bicyclic g-lactam unit of dihydropyrrolo[2,1a]isoquinolones depends on the nature of the nucleophile and the substituent at the angular position.
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The synthesis of DITOX, both in racemic and enantioenriched forms, was accomplished via sulfur oxidation of 1,3-dithiane or 2-acyl-1,3-dithiane derivatives, using chiral oxaziridines for the asymmetric process. The conjugate addition reaction of the α-sulfinyl carbanion derived from DITOX, prepared by deprotonation using the mixture of bases NaHMDS/n-BuLi, to the bicyclic γ-lactam unit of C-10b substituted dihydropyrrolo[2,1-a]isoquinolones led diastereoselectively to the corresponding trans isomer.
Fused pyridine derivatives R 0450 Stereocontrolled Conjugate Additions to Dihydroindolizinone Systems. Synthesis of Enantiopure Polysubstituted Tetrahydropyrrolo[2,1-a]isoquinolones. -Conjugate additions of various nucleophiles to indolizine derivatives (I), (IV) and (VII) are investigated with a view to the interesting medicinal properties of pyrrolo[2,1-a]isoquinolines. With exception of sulfur-stabilized carbanions, all additions require activation of the lactam by an ester group at C-2. The stereoselectivity depends on the nature of the angular substituent and the nucleophile. -(CAMARERO, C.; GONZALEZ-TEMPRANO, I.; GOMEZ-SANJUAN, A.; ARRASATE, S.; LETE*, E.; SOTOMAYOR, N.; Tetrahedron 65 (2009) 29-30, 5787-5798; Dep. Quim. Org., Fac. Cienc. Tecnol., Univ. Pais Vasco, E-48080 Bilbao, Spain; Eng.) -Nuesgen 46-150
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