- Lipase catalysis in the preparation of 3-(1-amino-3-butenyl)pyridine enantiomers
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The kinetic resolution of 1-(3-pyridyl)buten-3-ylamine with activated and non-activated acyl donors and Burkholderia cepacia lipase (lipase PS-D) under dry conditions has been studied. The N-acylation in isopropyl acetate (E >100) and the acidic hydrolysi
- Hietanen, Ari,Saloranta, Tiina,Leino, Reko,Kanerva, Liisa T.
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p. 1629 - 1632
(2013/02/22)
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- Asymmetric synthesis of δ-substituted α,β-unsaturated δ-lactams by ring closing metathesis of enantiomerically pure N-acryloyl-homoallylic amines
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(Chemical Equation Presented) Optically pure secondary homoallylic amines, obtained by highly diastereoselective addition of allylmetal reagents to imines derived from chiral amines, were N-dealkylated, and the primary amines were converted to N-acryloyl
- Fiorelli, Claudio,Savoia, Diego
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p. 6022 - 6028
(2008/02/10)
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- Enantioselective transfer aminoallylation: Synthesis of optically active homoallylic primary amines
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A camphorquinone-derived chiral homoallylic amine was found to react with various aldehydes via imine formation and asymmetric 2-azonia-Cope rearrangement to give optically active homoallylic primary amines. A practical level of enantioselectivity with hi
- Sugiura, Masaharu,Mori, Chieko,Kobayashi, Shu
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p. 11038 - 11039
(2007/10/03)
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- Efficient enantiomeric synthesis of pyrrolidine and piperidine alkaloids from tobacco
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An enantiomeric synthesis of six piperidine and pyrrolidine alkaloids, (S)-nornicotine 1, (S)-nicotine 2, (S)-anatabine 3, (S)-N-methylanatabine 4, (S)-anabasine 5, and (S)-N-methylanabasine 6, known as natural products in tobacco, was established from a common chiral homoallylic (S)-3-(1-azidobut-3-enyl)-pyridine 15. An intramolecular hydroboration-cycloalkylation of the homoallylic azide intermediate 15 served as the key step in the pyrrolidine ring formation. A ring closing metathesis reaction (RCM) of a diethylenic amine intermediate (S)-allyl-(1-pyridin-3-yl-but-3-enyl)-carbamic acid benzyl ester 20 served as the key step in the piperidine ring formation. From the commercially available 3-pyridinecarboxaldehyde 13, a short and convenient enantiomeric synthesis of tobacco alkaloids is described: (S)-nornicotine I (5 steps, with an overall yield of 70%), (S)-hicotine 2 (6 steps, 65%), (S)-anatabine 3 (8 steps, 30%), (S)-N-methylanatabine 4 (8 steps, 25%), (S)-anabasine 5 (8 steps, 35%), and (S)-N-methylanabasine 6 (8 steps, 25%).
- Felpin,Girard,Vo-Thanh,Robins,Villieras,Lebreton
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p. 6305 - 6312
(2007/10/03)
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- Total synthesis of (S)-anabasine and (S)-anatabine
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A chiral synthesis of (S)-anabasine and (S)-anatabine from 3-pyridinecarboxaldehyde, via a ring closing metathesis reaction (RCM) as the key step, is reported in 8 steps for both products with overall yields of 35% and 30%, respectively.
- Felpin,Vo-Thanh,Robins,Villieras,Lebreton
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p. 1646 - 1648
(2007/10/03)
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