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Synfacts 2010(6): 0709-0709  
DOI: 10.1055/s-0029-1220005
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Organocatalytic Carbocyclizations

Contributor(s): Benjamin List, Ilija Čorić
first article: S. Rendler, D. W. C. MacMillan*, second article: R. R. Knowles, S. Lin, E. N. Jacobsen*
Princeton University, USA and Harvard University, Cambridge, USA
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Publication History

Publication Date:
20 May 2010 (online)

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Significance

The research groups of MacMillan and Jacobsen have developed examples of organocatalytic carbocyclizations. Rendler and MacMillan employed organo-SOMO catalysis for cyclizations of polyene aldehydes (e.g., 3). Poly­cycles (e.g., 4) were obtained in good yields and enantioselectivity with 30 mol% of secondary amine catalyst 1. Jacobsen and co-workers developed thiourea catalyst 2 which effects poly­cyclization of hydroxylactams (e.g., 5). Polycycles (e.g., 6) were obtained in moderate to good yields and enantiomeric ratios up to 97:3.