Diastereoselective synthesis of aryl and alkyl trans-glycidic amides from pseudoephedrine-derived sulfonium salt. Chemospecific exo-tet ring closure for morpholin-3-ones
A regiospecific and high diastereoselective synthesis of trans-glycidic amides coming from a common pseudoephedrine sulfonium salt 2 precursor is presented. This is the first example in where the diastereoselectivity is controlled by a chiral noncyclic amide fragment. The epoxidation reaction provid...
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| Published in | Tetrahedron Vol. 68; no. 49; pp. 10252 - 10256 |
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| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
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Elsevier Ltd
09.12.2012
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| Abstract | A regiospecific and high diastereoselective synthesis of trans-glycidic amides coming from a common pseudoephedrine sulfonium salt 2 precursor is presented. This is the first example in where the diastereoselectivity is controlled by a chiral noncyclic amide fragment. The epoxidation reaction provides alkyl or aryl glycidic amides in good to excellent yields and exclusive trans selectivity. Finally, through of a chemospecific 6-exo-tet ring closure of trans-epoxyamides we access to morpholin-3-ones densely functionalized with excellent chemical and stereochemical yields.
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| AbstractList | A regiospecific and high diastereoselective synthesis of trans-glycidic amides coming from a common pseudoephedrine sulfonium salt 2 precursor is presented. This is the first example in where the diastereoselectivity is controlled by a chiral noncyclic amide fragment. The epoxidation reaction provides alkyl or aryl glycidic amides in good to excellent yields and exclusive trans selectivity. Finally, through of a chemospecific 6-exo-tet ring closure of trans-epoxyamides we access to morpholin-3-ones densely functionalized with excellent chemical and stereochemical yields. A regiospecific and high diastereoselective synthesis of trans-glycidic amides coming from a common pseudoephedrine sulfonium salt 2 precursor is presented. This is the first example in where the diastereoselectivity is controlled by a chiral noncyclic amide fragment. The epoxidation reaction provides alkyl or aryl glycidic amides in good to excellent yields and exclusive trans selectivity. Finally, through of a chemospecific 6-exo-tet ring closure of trans-epoxyamides we access to morpholin-3-ones densely functionalized with excellent chemical and stereochemical yields. [Display omitted] A regiospecific and high diastereoselective synthesis of trans-glycidic amides coming from a common pseudoephedrine sulfonium salt 2 precursor is presented. This is the first example in where the diastereoselectivity is controlled by a chiral noncyclic amide fragment. The epoxidation reaction provides alkyl or aryl glycidic amides in good to excellent yields and exclusive trans selectivity. Finally, through of a chemospecific 6-exo-tet ring closure of trans-epoxyamides we access to morpholin-3-ones densely functionalized with excellent chemical and stereochemical yields. (c) 2012 Elsevier Ltd. All rights reserved. |
| Author | Juárez, Jorge R. Gnecco, Dino Salazar, Ricardo Terán, Joel L. Mendoza, Angel Waksman, Noemí Aparicio, David M. Fores-Alamo, Marcos Orea, María L. |
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| Keywords | Morpholin-3-ones Diastereoselective Chemospecific trans-Glycidic amides 6-exo-tet Ring closure ASYMMETRIC-SYNTHESIS ACIDS ENANTIOSELECTIVE DARZENS REACTION ALDEHYDES EPOXIDATION STABILIZED SULFUR YLIDES PRACTICAL CHIRAL AUXILIARY CONDENSATION STEREOSELECTIVE-SYNTHESIS STEREOCONTROLLED SYNTHESIS Organic cation Exo stereoisomer Chiral compound Selectivity Stereochemistry Morpholine derivatives Regiospecificity Diastereoselectivity Alkaloid Pseudoephedrine Cyclization Functionalization Epoxidation Carboxamide Aromatic compound Chemical synthesis Sulfonium compound Oxygen nitrogen heterocycle |
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| References | Sarabia, Chammaa, García-Castro, Martín-Gálvez, Sarabia, Vivar-García, García-Castro, Martín-Ortiz (bib10) 2009; 76 Aggarwal, Richardson, Aggarwal, Charmant, Fuentes, Harvey, Hynd, Ohara, Picoul, Robiette, Smith, Vasse, Winn (bib9) 2003; 128 Aparicio, Terán, Gnecco, Galindo, Juárez, Orea, Mendoza, Aparicio, Terán, Roa, Gnecco, Juárez, Orea, Mendoza, Flores-Alamo, Micouin (bib11) 2009; 20 He, Liu, Ren, Lei, Gong, Doyle, Mckervey, Ye, Liu, Lv, Gong, López-Herrera, Sarabia-García, Pino-González (bib4) 2010; 352 For a review, see For description of epoxides coming from aromatic aldehydes see Díez, Núñez, Antoón, García, Moro, Garrido, Marcos, Nemoto, Kakei, Gnanadesikda, Tosaki, Ohshima, Shibasaki (bib1) 2008; 5 Sarabia, Martína-Gálvez, García-Castro, Chammaa, Sánchez-Ruiz, Tejón-Blanco, López-Herrera, Sarabia-García, Pino-González, Heras-López, Pino-González, Sarabia-García, López-Herrera, Valpuesta Fernández, Durante Lanes, López-Herrera, López Herrera, Pino González, Sarabia García, Heras López, Ortega Alcántara, Pedraza Cebrián (bib8) 2008; 73 Illa, Arshad, Ros, McGarrigle, Aggarwal, McGarrigle, Myers, Illa, Shaw, Riches, Aggarwal, Aggarwal, Hynd, Picoul, Vasse, Zhou, Hou, Dai, Xia, Tang (bib6) 2010; 132 Ratts, Yao, Valpuesta Fernández, Durante-Lanes, López-Herrera (bib7) 1966; 31 bib15 For the first use of pseudoephedrine as chiral auxiliary, see For other examples, see Myers, Gleason, Yoon, Kung, Chain, Myers (bib14) 1997; 119 Fuentes, Osorio, Quintero, Höpfl, Vázquez-Cabrera, Sartillo-Piscil (bib2) 2012; 77 Waser, Herchi, Müller, Herchl, Stiftinger, Waser (bib5) 2011; 9 bib16 Rosen, Tung, Speziale, Frazier, Arai, Tokumaru, Aoyama (bib3) 1991; Vol. 2 Sarabia, F (WOS:000270115300029) 2009 Arai, S (WOS:000189116200006) 2004; 45 Nemoto, T (WOS:000179661000019) 2002; 124 Vicario, JL (WOS:000223581900039) 2004; 6 Illa, O (WOS:000275085000044) 2010; 132 Anakabe, E (WOS:000172277200019) 2001; 2001 Chain, WJ (WOS:000243389000047) 2007; 9 McGarrigle, EM (WOS:000251583300013) 2007; 107 Vicario, JL (WOS:000087609100023) 2000; 65 Diez, D (WOS:000259447300001) 2008; 5 Sarabia, F (WOS:000289956900019) 2011; 76 RATTS, KW (WOS:A19667862300005) 1966; 31 Doyle, M. 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| Snippet | A regiospecific and high diastereoselective synthesis of trans-glycidic amides coming from a common pseudoephedrine sulfonium salt 2 precursor is presented.... |
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| SubjectTerms | 6-exo-tet Ring closure Amides Aromatic compounds Chemistry Chemistry, Organic Chemospecific Closures Diastereoselective Epoxidation Exact sciences and technology Fragmentation Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Morpholin-3-ones Organic chemistry Physical Sciences Precursors Preparations and properties Science & Technology Synthesis Tetrahedrons trans-Glycidic amides |
| Title | Diastereoselective synthesis of aryl and alkyl trans-glycidic amides from pseudoephedrine-derived sulfonium salt. Chemospecific exo-tet ring closure for morpholin-3-ones |
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