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Efficient synthesis of optically active 4-nitro-cyclohexanones via bifunctional thiourea-base catalyzed double-Michael addition of nitromethane to dienones.
Chem Commun (Camb). 2011 Apr 07; 47(13):3992-4.CC

Abstract

Thiourea-modified cinchona alkaloids as bifunctional catalysts and a base could catalyze a stepwise [5+1] cyclization of divinyl ketones with nitromethane via double Michael additions, furnishing optically active 4-nitro-cyclohexanones with good yields, excellent diastereoselectivities (>20 : 1) and high enantiomeric ratios (up to 97 : 3).

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Publisher Full Text (DOI)

Authors+Show Affiliations

Wu B
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China.
Liu GG
No affiliation info available
Li MQ
No affiliation info available
Zhang Y
No affiliation info available
Zhang SY
No affiliation info available
Qiu JR
No affiliation info available
Xu XP
No affiliation info available
Ji SJ
No affiliation info available
Wang XW
No affiliation info available

MeSH

CatalysisCinchona AlkaloidsCyclohexanonesMethaneNitro CompoundsNitroparaffinsThiourea

Pub Type(s)

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

Language

eng

PubMed ID

21331389

Citation

Wu, Bin, et al. "Efficient Synthesis of Optically Active 4-nitro-cyclohexanones Via Bifunctional Thiourea-base Catalyzed double-Michael Addition of Nitromethane to Dienones." Chemical Communications (Cambridge, England), vol. 47, no. 13, 2011, pp. 3992-4.
Wu B, Liu GG, Li MQ, et al. Efficient synthesis of optically active 4-nitro-cyclohexanones via bifunctional thiourea-base catalyzed double-Michael addition of nitromethane to dienones. Chem Commun (Camb). 2011;47(13):3992-4.
Wu, B., Liu, G. G., Li, M. Q., Zhang, Y., Zhang, S. Y., Qiu, J. R., Xu, X. P., Ji, S. J., & Wang, X. W. (2011). Efficient synthesis of optically active 4-nitro-cyclohexanones via bifunctional thiourea-base catalyzed double-Michael addition of nitromethane to dienones. Chemical Communications (Cambridge, England), 47(13), 3992-4. https://doi.org/10.1039/c0cc05418f
Wu B, et al. Efficient Synthesis of Optically Active 4-nitro-cyclohexanones Via Bifunctional Thiourea-base Catalyzed double-Michael Addition of Nitromethane to Dienones. Chem Commun (Camb). 2011 Apr 7;47(13):3992-4. PubMed PMID: 21331389.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Efficient synthesis of optically active 4-nitro-cyclohexanones via bifunctional thiourea-base catalyzed double-Michael addition of nitromethane to dienones. AU - Wu,Bin, AU - Liu,Guo-Gui, AU - Li,Mei-Qiu, AU - Zhang,Yong, AU - Zhang,Shao-Yun, AU - Qiu,Jun-Ru, AU - Xu,Xiao-Ping, AU - Ji,Shun-Jun, AU - Wang,Xing-Wang, Y1 - 2011/02/17/ PY - 2011/2/19/entrez PY - 2011/2/19/pubmed PY - 2011/7/20/medline SP - 3992 EP - 4 JF - Chemical communications (Cambridge, England) JO - Chem Commun (Camb) VL - 47 IS - 13 N2 - Thiourea-modified cinchona alkaloids as bifunctional catalysts and a base could catalyze a stepwise [5+1] cyclization of divinyl ketones with nitromethane via double Michael additions, furnishing optically active 4-nitro-cyclohexanones with good yields, excellent diastereoselectivities (>20 : 1) and high enantiomeric ratios (up to 97 : 3). SN - 1364-548X UR - https://www.unboundmedicine.com/medline/citation/21331389/Efficient_synthesis_of_optically_active_4_nitro_cyclohexanones_via_bifunctional_thiourea_base_catalyzed_double_Michael_addition_of_nitromethane_to_dienones_ L2 - https://doi.org/10.1039/c0cc05418f DB - PRIME DP - Unbound Medicine ER -