Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 23, Pages 7030-7038Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201000483
Keywords
camphor; citronellal; Michael addition; nitroalkenes; organocatalysis
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Funding
- National Science Council of the Republic of China [NSC 96-2113M-003-005-MY3, NSC 98-2119M-003-003]
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Practical and convenient synthetic routes have been developed for the synthesis of a new class of pyrrolidinyl camphor derivatives (7a-h). These novel compounds were screened as catalysts for the direct Michael addition of symmetrical alpha,alpha-disubstituted aldehydes to beta-nitroalkenes. When this asymmetric transformation was catalyzed by organocatalyst 7f, the desired Michael adducts were obtained in high chemical yields, with high to excellent stereoselectivities (up to 98:2 diastereomeric ratio (d.r.) and 99% enantio-meric excess (ee)). The scope of the catalytic system was expanded to encompass various aldehydes and ketones as the donor sources. The synthetic application was demonstrated by the synthesis of a tetrasubstituted-cyclohexane derivative from (S)-citronellal, with high stereoselectivity.
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