Efficient and highly diastereoselective preparation of a myrtenal derived bis-sulfoxide and its preliminary evaluation as chiral acyl donor

• Published in: Tetrahedron letters Vol. 46; no. 19; pp. 3297 - 3300
• Main Authors: Vargas-Dı́az, M. Elena, Lagunas-Rivera, Selene, Joseph-Nathan, Pedro, Tamariz, Joaquı́n, Zepeda, L. Gerardo
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 09.05.2005; Elsevier
• Subjects: (1 R)-(−)-Myrtenal; Acyl donor; Bis-sulfoxide; Chemistry; Chemistry, Organic; Chiral auxiliary; Diastereoselective nucleophilic addition; Physical Sciences; Science & Technology; Bis-sulfoxide; Diastereoselective nucleophilic addition; Chiral auxiliary; (1 R)-(−)-Myrtenal; Acyl donor; (1R)-(-)-myrtenal; CYCLOADDITION REACTIONS; ASYMMETRIC-SYNTHESIS; TRANS-1,3-DITHIANE 1,3-DIOXIDE; ENANTIOSELECTIVE SYNTHESIS; NUCLEOPHILIC ADDITIONS; diastereoselective nucleophilic addition; CARBONYL-COMPOUNDS; ALDEHYDES; bis-sulfoxide; acyl donor; chiral auxiliary; ANION REACTIONS; BETA-HYDROXY-ACIDS; KETENE EQUIVALENT
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2005.03.104

[Display omitted] Treatment of disulfide 7 with NaIO 4 in EtOH at rt gave monosulfoxide 8 (95%), while at 50 °C it gave trans-bis-sulfoxide 6a (84%, >99% de). In contrast, treatment of 7 with MCPBA gave bis-sulfone 9 (95%). The anion of 6a reacted with benzaldehyde affording carbinol 10 (76%, >99% de). The absolute configuration of 8 , 6a , and 10 was established by single crystal X-ray diffraction analyses.