TY - JOUR
T1 - Efficient and highly diastereoselective preparation of a myrtenal derived bis-sulfoxide and its preliminary evaluation as chiral acyl donor
AU - Vargas-Díaz, M. Elena
AU - Lagunas-Rivera, Selene
AU - Joseph-Nathan, Pedro
AU - Tamariz, Joaquín
AU - Zepeda, L. Gerardo
N1 - Funding Information:
This work was supported by CONACyT (Grants 35013E and 44157-Q) and CGPI-IPN (Grants 20030702 and 20040199). M.E.V.D. and S.L.R. thank CGPI/IPN (PIFI) and CONACyT (125225 and 165282, respectively) postgraduate fellowships.
PY - 2005/5/9
Y1 - 2005/5/9
N2 - Treatment of disulfide 7 with NaIO4 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.
AB - Treatment of disulfide 7 with NaIO4 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.
KW - (1R)-(-)-Myrtenal
KW - Acyl donor
KW - Bis-sulfoxide
KW - Chiral auxiliary
KW - Diastereoselective nucleophilic addition
UR - http://www.scopus.com/inward/record.url?scp=17144411814&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2005.03.104
DO - 10.1016/j.tetlet.2005.03.104
M3 - Artículo
SN - 0040-4039
VL - 46
SP - 3297
EP - 3300
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 19
ER -