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Enantioselective Synthesis of Indoloquinolizidines via Asymmetric Catalytic Hydrogenation/Lactamization of Imino Diesters.
- Source :
-
Journal of Organic Chemistry . 12/6/2013, Vol. 78 Issue 23, p12009-12017. 9p. - Publication Year :
- 2013
-
Abstract
- We have developed a highly efficient cascade sequence for asymmetric synthesis of indoloquinolizidines with absolute control of cis-H2/H12b relative geometry in good to excellent yields and excellent enantioselectivities. This cascade was triggered by the Ru(ll)-TsDPEN-catalyzed asymmetric transfer hydrogenation of imino diesters, with subsequent spontaneous lactaniization with discrimination between the two diastereotopic 2-allcoxy-2-oxoethyl groups. The synthetic utility of this strategy was demonstrated by the asymmetric preparation of dihydrocorynantheol, geissaschizol, and isogeissoschizol. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 78
- Issue :
- 23
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 93372577
- Full Text :
- https://doi.org/10.1021/jo4020547