ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. URL: https://www.sciencedirect.com/science/article/pii/B9780080977423008168, URL: https://www.sciencedirect.com/science/article/pii/B9780128009345000116, URL: https://www.sciencedirect.com/science/article/pii/B9780444519672001124, URL: https://www.sciencedirect.com/science/article/pii/B9780081007556000090, URL: https://www.sciencedirect.com/science/article/pii/B9780128052549000128, URL: https://www.sciencedirect.com/science/article/pii/B9780124077744000017, URL: https://www.sciencedirect.com/science/article/pii/B9780124115651000032, URL: https://www.sciencedirect.com/science/article/pii/B9780123965271000036, URL: https://www.sciencedirect.com/science/article/pii/B9780444632814000124, Comprehensive Organic Synthesis II (Second Edition). Scheme 12.13. 6.86±0.009 µM in MDA-MB-231. derivatives depicted significant cytotoxicity in cancer cell lines but not in normal human This novel analogue class was analyzed for its antiproliferative and actin binding properties. b: (i) 86, –90 °C, 73%. was very efficient for the reduction of azides5b, of zinc and ammonium chloride was probably more efficient for the reduction (R)-2-Azidoesters and their derived (R)-2-azido acids are readily prepared from common amino acids by an inversion methodology that employs (S)-2-nosyloxyesters as key intermediates. Staudinger reduction of the N3 group, Boc protection, and protection of the phenolic OH with BnBr gave mono-boc phenacylamine in good yield. Considering zinc is more reactive than ferrum, we proposed that the combination Reductive ligation of RSNOs with phosphines. (ii) (S)-o-tol-CBS (81, 25 mol%), TfOH (20 mol%), 5-trimethylsilylcyclopentadiene (74), CH2Cl2, –78 °C, 78%, 93% ee. 30 days to view or download: Note on the Synthesis of an Optically Active ACE Inhibitor with Amino-oxo-benzazepine-1-alkanoic-Acid Structure by Means of an Enantioconvergent Crystallization-Based ResolutionAn enantioselective synthesis of the potent angiotensin-converting enzyme inhibitor (1′S,3S)-3-[(1′-(ethoxy-carbonyl)-3′-phenylpropyl)amino]-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic acid hydrochloride (3) is described which user a crystallization-based resolution of a racemic amino intermediate with concomitant racemization of the unwanted enantiomer. R 3 P=NR' + H 2 O → R 3 P=O + R'NH 2 The overall conversion is a mild method of reducing an azide to an amine. Asymmetric Synth., Chengdu Inst. The reactive azaylide nucleophilically attacks the adjacent ester group forming a tetrahedral intermediate that decomposes with alcohol release and a phosphonium-like product (6, Scheme 11.4).