Regiospecific additions of hydrazoic acid and benzylamine to 1-(arylsulfonyl)bicyclo[1.1.0]Butanes. Application to the synthesis of cis and trans 2,7-methanoglutamic acids |
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| Institution: | 1. Institute of Applied Problems of Physics, NAS of Armenia, 25 Nersessyan Str., 0014 Yerevan, Armenia;2. Institute of Mineralogy and Crystallography, University of Vienna, Althanstr. 14, A-1090 Vienna, Austria;1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 Moscow, Russian Federation;2. Ivane Javakhishvili Tbilisi State University, 0179 Tbilisi, Georgia;1. Université LUNAM, Nantes Université, CNRS, Chimie et Interdisciplinarité: Synthèse, Analyse, Modélisation (CEISAM), UMR 6230, 2 rue de la Houssinière, 44322, Nantes cedex 3, France;2. Department of Chemistry, KU Leuven, Celestijnenlaan, 200F, B-3001, Leuven, Belgium;1. Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, Fujian 350108, China;2. College of Chemistry and Institute of Green Catalysis, Zhengzhou University, Zhengzhou, Henan 450001, China;3. School of Chemistry and Chemical Engineering, State Key Laboratory of Antiviral Drugs, Henan Normal University, Xinxiang, Henan 453007, China |
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| Abstract: | Addition of hydrazoic acid or benzylamine to 1-(arylsulfonyl) bicyclobutanes introduces the nitrogen nucleophlle at position 3 of the derived cyclobutane, even when a carboxyl derivative is present at this position as a second activating group. Precursors of α-amino cyclobutane carboxylic acids may thus be obtained and these can be further transformed to the title diacids via carbonylation α to the sulfone and reduction. |
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