Synthesis of 1,3-amino alcohol derivatives via a silicon-mediated ring-opening of substituted piperidines.
作者： W. Stephen McCall , Daniel L. Comins
DOI: 10.1021/OL9010757
关键词:
摘要: Multisubstituted piperidines containing a trimethylsilylmethyl group at C-2 can be opened regioselectively with TBAF and cyanogen bromide. The ring-opened products contain synthetically useful cyanamide terminal alkene functional groups. This method is for the stereoselective synthesis of alkylamine derivatives multiple chiral centers.
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sci-hub.se 参考文章(17)
D.L. Comins, S. O’Connor, R.S. Al-awar, Pyridines and their Benzo Derivatives: Reactivity at the Ring Comprehensive Heterocyclic Chemistry III. ,vol. 7, pp. 41- 99 ,(2008) , 10.1016/B978-008044992-0.00602-7
W. Stephen McCall, Teresa Abad Grillo, Daniel L. Comins, Stereoselective Synthesis of Acyclic Amino Alcohols via von Braun Ring Opening of Chiral Piperidines Organic Letters. ,vol. 10, pp. 3255- 3257 ,(2008) , 10.1021/OL801123X
Daniel L. Comins, Donald H. LaMunyon, Grignard addition to 1-acyl salts of chiral 4-alkoxypyridines. A new enantioselective preparation of 2-alkyl-2,3-dihydro-4-pyridones Tetrahedron Letters. ,vol. 35, pp. 7343- 7346 ,(1994) , 10.1016/0040-4039(94)85309-6
Daniel L. Comins, Sajan P. Joseph, R. Richard Goehring, Asymmetric synthesis of 2-alkyl(aryl)-2,3-dihydro-4-pyridones by addition of Grignard reagents to chiral 1-acyl-4-methoxypyridinium salts Journal of the American Chemical Society. ,vol. 116, pp. 2574- 2576 ,(1990) , 10.1021/JA00090A019
Herbert Waldmann, ASYMMETRIC HETERO-DIELS-ALDER REACTIONS Synthesis. ,vol. 1994, pp. 535- 551 ,(1994) , 10.1055/S-1994-25519
Daniel L Connns, Jack D Brown, Additiom of Grignard reagents to 1-acyl-4-methoxypyridinum salts. An approach to the synthesis of quinolizidinones. Tetrahedron Letters. ,vol. 27, pp. 4549- 4552 ,(1986) , 10.1016/S0040-4039(00)85000-5
Stéphane Chambert, François Thomasson, Jean-Luc Décout, 2-Trimethylsilylethyl sulfides in the von Braun cyanogen bromide reaction: selective preparation of thiocyanates and application to nucleoside chemistry. Journal of Organic Chemistry. ,vol. 67, pp. 1898- 1904 ,(2002) , 10.1021/JO016200Q
W. Stephen McCall, Teresa Abad Grillo, Daniel L. Comins, N-acyldihydropyridones as synthetic intermediates. A stereoselective synthesis of acyclic amino alcohols containing multiple chiral centers. Journal of Organic Chemistry. ,vol. 73, pp. 9744- 9751 ,(2008) , 10.1021/JO802029Y
Dimitar B. Gotchev, Daniel L. Comins, Synthetic studies toward (-)-FR901483 using a conjugate allylation to install the C-1 quaternary carbon. Journal of Organic Chemistry. ,vol. 71, pp. 9393- 9402 ,(2006) , 10.1021/JO061677T
Damian W. Young, Daniel L. Comins, Tandem directed lithiations of N-Boc-1,2-dihydropyridines toward highly functionalized 2,3-dihydro-4-pyridones. Organic Letters. ,vol. 7, pp. 5661- 5664 ,(2005) , 10.1021/OL052313A