Nitrosocarbonyl Carbohydrate Derivatives: Hetero Diels–Alder and Ene Reaction Products for Useful Organic Synthesis

Abstract

The generation and trapping of two new nitrosocarbonyl intermediates bearing carbohydrate-based chiral substituents is achieved by the mild oxidation of the corresponding nitrile oxides with tertiary amine N-oxides. Their capture with suitable dienes and alkenes afforded the corresponding hetero Diels–Alder cycloadducts and ene adducts from fair to excellent yields. The entire methodology looks highly promising by the easy conversion of aldoximes into hydroxymoyl halides, widening the access to nitrosocarbonyls, versatile tools in organic synthesis.

Key words

nitrosocarbonyl - hetero Diels–Alder reactions - ene reactions - nitrile oxides - synthetic applications

Publication History

Received: 06 July 2020

Accepted after revision: 08 August 2020

Article published online:
22 September 2020

• References

• 1a Memeo MG, Quadrelli P. Chem. Rev. 2017; 117: 2108
• 1b For a latest report on nitrosocarbonyl generation, see: Uraoka S, Shinohara I, Shimizu H, Noguchi K, Yoshimura A, Zhdankin VV, Saito A. Eur. J. Org. Chem. 2018; 6199
• 2 Cohen AD, Zeng B.-B, King SB, Toscano JP. J. Am. Chem. Soc. 2003; 125: 1444
• 3 Quadrelli P, Moiola M. In Modern Applications of Cycloaddition Chemistry . Quadrelli P. Elsevier; Amsterdam: 2019: 1-83
• 4 Chiu D.-C, Lin T.-C, Huang W.-I, Cheng T.-J, Tsaic K.-C, Fang J.-M. Org. Biomol. Chem. 2017; 15: 9910
• 5 Haines AH, Morley C, Murrer BA. J. Med. Chem. 1989; 32: 742
• 6 Zhang P, Wei C, Wang E, Wanga W, Liu M, Yin Q, Chen H, Wang K, Li X, Zhang J. Carbohydr. Res. 2012; 351: 7
• 7 Tronchet JM. J, Barbalat-Rey F, Le-Hong NM, Burger U. Carbohydr. Res. 1973; 29: 297
• 8 Schmid CR, Bryant JD, Dowlatzedah M, Phillips JL, Prather DE, Schantz RD, Sear NL, Vianco CS. J. Org. Chem. 1991; 56: 4056
• 9 Liu KC, Shelton BR, Howe RK. J. Org. Chem. 1980; 45: 3916
• 10 Quadrelli P, Mella M, Gamba Invernizzi A, Caramella P. Tetrahedron 1999; 55: 10497
• 11 Quadrelli P, Campari G, Mella M, Caramella P. Tetrahedron Lett. 2000; 41: 2019
• 12 Quadrelli P, Mella M, Caramella P. Tetrahedron Lett. 1998; 39: 3233
• 13 Hameed KK, Amin AA, Hussain FH. S, Memeo MG, Moiola M, Quadrelli P. Synthesis 2019; 51: 1383
• 14a Quadrelli P, Mella M, Piccanello A, Romano S, Caramella P. J. Org. Chem. 2007; 72: 1807
• 14b Quadrelli P, Romano S, Piccanello A, Caramella P. J. Org. Chem. 2009; 74: 2301

For ‘cis effect’, see also:
• 14c Leach AG, Houk KN. Chem. Commun. 2002; 1243
• 14d Clennan EL. Tetrahedron 2000; 56: 9151
• 15a Adam W, Krebs O. Chem. Rev. 2003; 103: 4131
• 15b Leach AG, Houk KN. Org. Biomol. Chem. 2003; 1: 1389
• 15c Leach AG, Houk KN. J. Am. Chem. Soc. 2002; 124: 14821
• 15d Orfanopoulos M, Bellarmine Grdina MSr, Stephenson LM. J. Am. Chem. Soc. 1979; 101: 275
• 15e Lu X. Org. Lett. 2004; 6: 2813
• 16a Adam W, Krebs O, Orfanopoulos M, Stratakis M, Vougioukalakis GC. J. Org. Chem. 2003; 68: 2420
• 16b See also: Adam W, Bottke N, Engels B, Krebs O. J. Am. Chem. Soc. 2001; 123: 5542
• 16c Singleton DA, Hang C. J. Am. Chem. Soc. 1999; 121: 11885
• 16d Vougioukalakis GC, Orfanopoulos M. Synlett 2005; 713
• 17 Gramera RE, Bruce RM, Hirase S, Whistler RL. J. Org. Chem. 1963; 28: 1401
• 18 Wolfrom ML, Hanessian S. J. Org. Chem. 1962; 27: 1800
• 19 Tronchet JM. J, Martin O, Zumwald J.-B, Le-Hong N, Perret F. Helv. Chim. Acta 1975; 58: 1735
• 20 Quadrelli P, Mella M, Caramella P. Tetrahedron Lett. 1999; 40: 797
• 21 Ma D, Xia C, Tian H. Tetrahedron Lett. 1999; 40: 8915
• 22 Defoin A, Pires J, Tissot I, Tschamber T, Bur D, Zehnder M, Streith J. Tetrahedron: Asymmetry 1991; 2: 1209
• 23 Zhang Q, Cao R, Liu A, Lei S, Li Y, Yang J, Li S, Xiao J. Bioorg. Med. Chem. Lett. 2017; 27: 4061
• 24 Amdouni H, Robert G, Driowya M, Furstoss N, Métier C, Dubois A, Dufies M, Zerhouni M, Orange F, Lacas-Gervais S, Bougrin K, Martin AR, Auberger P, Benhida R. J. Med. Chem. 2017; 60: 1523