Comparing and taming the reactivity of HWE and Wittig reagents with cyclic hemiacetals
作者： Jokin Carrillo , Anna M. Costa , Mireia Sidera , Jaume Vilarrasa
DOI: 10.1016/J.TETLET.2011.07.121
关键词: Amide 、 Morpholine 、 Wittig reaction 、 Organic chemistry 、 Lactol 、 Chemistry 、 Reactivity (chemistry) 、 Hemiacetal 、 Reagent 、 Phosphorane
摘要: Abstract A practical solution to the formation of mixtures E/Z and open/cyclic isomers in reaction (2R,4S)-4-hydroxy-2-methylpentanal (as its hemiacetal, a lactol) with conjugated phosphoranes (stabilised Wittig reagents) Horner–Wadsworth–Emmons reagents is disclosed. The HWE has strong bias give oxolanes. On other hand, stabilised unsaturated carboxyl derivatives configuration E (major) oxolanes (minor); latter can be avoided by addition CF3CH2OH or using morpholine amide phosphorane.
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sci-hub.se 参考文章(49)
Benjamin E. Stephens, Fei Liu, A Regio- and Diastereoselective Intramolecular Nitrone Cycloaddition for Practical 3- and 2,3-Disubstituted Piperidine Synthesis from γ-Butyrolactone Journal of Organic Chemistry. ,vol. 74, pp. 254- 263 ,(2009) , 10.1021/JO8018285
M. F. Semmelhack, Nan Zhang, Stereoselective formation of tetrahydrofuran rings via intramolecular alkoxycarbonylation of hydroxyalkenes Journal of Organic Chemistry. ,vol. 54, pp. 4483- 4485 ,(1989) , 10.1021/JO00280A003
Bruce E. Maryanoff, Allen B. Reitz, The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspects Chemical Reviews. ,vol. 89, pp. 863- 927 ,(1989) , 10.1021/CR00094A007
Won Hee Kim, Ah-Young Park, Jin-Ah Kang, Jungsu Kim, Jin-Ah Kim, Hyung-Rock Lee, Pusoon Chun, Jungwon Choi, Chong-Kyo Lee, Lak Shin Jeong, Hyung Ryong Moon, None, First synthesis of 2′-oxabicyclo[3.1.0]hexyl nucleosides with a north conformation Tetrahedron. ,vol. 66, pp. 1706- 1715 ,(2010) , 10.1016/J.TET.2010.01.014
Liang Lu, Wei Zhang, Rich G. Carter, Total synthesis of cytotoxic macrolide amphidinolide B1 and the proposed structure of amphidinolide B2. Journal of the American Chemical Society. ,vol. 130, pp. 7253- 7255 ,(2008) , 10.1021/JA803012N
Chenze Qi, Yijun Du, Yueqing Lu, Xudong Sun, Xian-Man Zhang, Equilibrium acidities and homolytic bond dissociation enthalpies of the acidic C-H bonds in phosphonates and related phosphorus containing compounds. Journal of Organic Chemistry. ,vol. 74, pp. 8078- 8085 ,(2009) , 10.1021/JO901270P
Carlo Bonini, Lucia Chiummiento, Margherita De Bonis, Maria Funicello, Paolo Lupattelli, Synthesis of a first thiophene containing analog of the HIV protease inhibitor nelfinavir Tetrahedron Letters. ,vol. 45, pp. 2797- 2799 ,(2004) , 10.1016/J.TETLET.2004.02.026
Jiro Motoyoshiya, Tatsuya Kusaura, Keisuke Kokin, Sei-ichi Yokoya, Yutaka Takaguchi, Susumu Narita, Hiromu Aoyama, The Horner–Wadsworth–Emmons reaction of mixed phosphonoacetates and aromatic aldehydes: geometrical selectivity and computational investigation Tetrahedron. ,vol. 57, pp. 1715- 1721 ,(2001) , 10.1016/S0040-4020(01)00007-2
Anna Olivella, Carles Rodríguez-Escrich, Fèlix Urpí, Jaume Vilarrasa, Michael reactions of titanium enolates of glycolic acid derivatives with the Weinreb and morpholine amides of acrylic acid. Journal of Organic Chemistry. ,vol. 73, pp. 1578- 1581 ,(2008) , 10.1021/JO702240N
Bhimapaka China Raju, Pathi Suman, None, New and Facile Approach for the Synthesis of (E)‐α,β‐Unsaturated Esters and Ketones Chemistry: A European Journal. ,vol. 16, pp. 11840- 11842 ,(2010) , 10.1002/CHEM.201000883