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Pyrrolidinyl-camphor derivatives as a new class of organocatalyst for direct asymmetric Michael addition of aldehydes and ketones to beta-nitroalkenes.
Chemistry. 2010 Jun 18; 16(23):7030-8.C

Abstract

Practical and convenient synthetic routes have been developed for the synthesis of a new class of pyrrolidinyl-camphor derivatives (7 a-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 7 f, 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 % enantiomeric 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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Publisher Full Text (DOI)

Authors+Show Affiliations

Ting YF
Department of Chemistry, National Taiwan Normal University, Taipei, 116, ROC, Taiwan.
Chang C
No affiliation info available
Reddy RJ
No affiliation info available
Magar DR
No affiliation info available
Chen K
No affiliation info available

MeSH

Acyclic MonoterpenesAldehydesAlkenesCamphorCatalysisCyclohexanesKetonesMolecular StructureMonoterpenesNitro CompoundsPyrrolidinesStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

20455225

Citation

Ting, Ying-Fang, et al. "Pyrrolidinyl-camphor Derivatives as a New Class of Organocatalyst for Direct Asymmetric Michael Addition of Aldehydes and Ketones to Beta-nitroalkenes." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 16, no. 23, 2010, pp. 7030-8.
Ting YF, Chang C, Reddy RJ, et al. Pyrrolidinyl-camphor derivatives as a new class of organocatalyst for direct asymmetric Michael addition of aldehydes and ketones to beta-nitroalkenes. Chemistry. 2010;16(23):7030-8.
Ting, Y. F., Chang, C., Reddy, R. J., Magar, D. R., & Chen, K. (2010). Pyrrolidinyl-camphor derivatives as a new class of organocatalyst for direct asymmetric Michael addition of aldehydes and ketones to beta-nitroalkenes. Chemistry (Weinheim an Der Bergstrasse, Germany), 16(23), 7030-8. https://doi.org/10.1002/chem.201000483
Ting YF, et al. Pyrrolidinyl-camphor Derivatives as a New Class of Organocatalyst for Direct Asymmetric Michael Addition of Aldehydes and Ketones to Beta-nitroalkenes. Chemistry. 2010 Jun 18;16(23):7030-8. PubMed PMID: 20455225.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Pyrrolidinyl-camphor derivatives as a new class of organocatalyst for direct asymmetric Michael addition of aldehydes and ketones to beta-nitroalkenes. AU - Ting,Ying-Fang, AU - Chang,Chihliang, AU - Reddy,Raju Jannapu, AU - Magar,Dhananjay R, AU - Chen,Kwunmin, PY - 2010/5/11/entrez PY - 2010/5/11/pubmed PY - 2010/9/15/medline SP - 7030 EP - 8 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 16 IS - 23 N2 - Practical and convenient synthetic routes have been developed for the synthesis of a new class of pyrrolidinyl-camphor derivatives (7 a-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 7 f, 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 % enantiomeric 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. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/20455225/Pyrrolidinyl_camphor_derivatives_as_a_new_class_of_organocatalyst_for_direct_asymmetric_Michael_addition_of_aldehydes_and_ketones_to_beta_nitroalkenes_ L2 - https://doi.org/10.1002/chem.201000483 DB - PRIME DP - Unbound Medicine ER -