An efficient organocascade quadruple reaction was conducted to synthesize a functionalized spiropolycyclic scaffold in high chemical yields (43-80%) and excellent levels of stereoselectivity (up to >19:1 dr and 99% ee). The quadruple reaction proceeded smoothly between 1,3-indanedione and aromatic aldehydes with concomitant desymmetrization of prochiral 4-substituted cyclohexanones through the Knoevenagel/Michael/aldol/aldol reaction sequence catalyzed by a bifunctional thiourea catalyst. Two of the formed products were transformed into spirocyclic epoxides containing four contiguous quaternary centers.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
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Gurubrahamam, R. (Contributor), Chen, K. (Contributor) & Chang, Y. (Contributor), Unknown Publisher, 2015 Jun 19
Chen, K. (Contributor), Chang, Y. (Contributor) & Gurubrahamam, R. (Contributor), Unknown Publisher, 2015 Jun 19