- On the synthesis of α-amino sulfoxides
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A synthetic study on the preparation of N-Boc α-amino sulfoxides has revealed an unexpected instability which is believed to be due to α-elimination of the sulfoxide to give an iminium ion. Full synthetic details are reported on two main synthetic routes: lithiation and sulfinate trapping of N-Boc heterocycles and oxidation of N-Boc α-amino sulfides. Six novel α-amino sulfoxides were successfully prepared and isolated. It is speculated that four other α-amino sulfoxides were synthesised but could not be isolated due to their propensity to α-eliminate the sulfoxide. Ultimately, a stable, cyclic N-Boc α-amino sulfoxide was prepared and this successful synthesis relied on the α-amino sulfoxide being part of a bicyclic [3.1.0] fused ring system that could not undergo α-elimination of the sulfoxide. the Partner Organisations 2014.
- Rayner, Peter J.,Gelardi, Giacomo,O'Brien, Peter,Horan, Richard A. J.,Blakemore, David C.
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p. 3499 - 3512
(2014/05/20)
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- Rhodium-catalyzed asymmetric hydroformylation of n-allvlamides: Highly enantioselective approach to β2-amino aldehydes
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(Figure Presented) You're having a lahf I The asymmetric hydroformylation (AHF) of allylic compounds, catalyzed by a rhodium-yanphos complex, is a direct and concise route to ss2-amino aldehydes, acids, and alcohols with excellent enantioselectivity (see scheme; TON =turnover number, acac = acetylacetonate).
- Zhang, Xiaowei,Cao, Bonan,Yu, Shichao,Zhang, Xumu
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supporting information; experimental part
p. 4047 - 4050
(2010/08/07)
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- Copper Cyanide-Catalyzed Palladium Coupling of N-tert-Butoxycarbonyl-Protected α-Lithio Amines with Aryl Iodides or Vinyl Iodides
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Treatment of (α-aminoalkyl)lithium reagents with aryl iodides in the presence of catalytic amounts of CuCN and PdCl2(PPh3)2 or [(p-MeOC6H4)3P]4Pd affords 2-aryl substituted amines in modest to good yields. The yields can be improved by use of softer ligands such as AsPh3 and SbPh3 or by use of bis(diphenylphosphino)ferrocene (dppf). Coupled products are obtained with electron-rich aryl iodides (XArI, X = Me, OMe), and the reaction fails with electron-poor aryl iodides (XArI, X = NO2, CO2Li). Treatment of the (α-aminoalkyl)lithium reagents with vinyl iodides and Pd(0)/dppf/ CuCN afforded the coupling products in low to modest yields.
- Karl Dieter,Li, ShengJian
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p. 7726 - 7735
(2007/10/03)
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- Palladium-Catalyzed Carbonylation. A New Synthesis of α-Methylene γ-, δ-, and ε-Lactams and -Lactones Including Bicyclic Lactams of Pyrrolizidine and Indolizidine Skeletons
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The insertion of carbon monoxide into vinyl halides bearing the secondary amine or alcohol with a catalytic amount of Pd(OAc)2 and PPh3 was realized to give five-, six-, and seven-membered lactams and lactones carrying α-methylene groups in fairly good yields.Bicyclic heterocycles, pyrrolizidine and indolizidine derivatives, were also synthesized from pyrrolidine and piperidine derivatives possessing vinyl halide groups in the side chain at the 2-position of the ring by means of palladium-catalyzed carbonylation.
- Mori, Miwako,Washioka, Yumiko,Urayama, Takao,Yoshiura, Kagari,Chiba, Katsumi,Ban, Yoshio
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p. 4058 - 4067
(2007/10/02)
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