Co-reporter:Christian S. Jungong, Alexei V. Novikov
Tetrahedron: Asymmetry 2013 Volume 24(2–3) pp:151-155
Publication Date(Web):15 February 2013
DOI:10.1016/j.tetasy.2012.12.002
The asymmetric C–H insertion of alkyldiazosulfones has been studied. High selectivity was achieved using a combination of a chiral catalyst and a chiral auxiliary (Rh2(S-pttl)4 and menthyl ester).(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl (2R,3R)-tetrahydro-3-methyl-2H-thiopyran-1,1-dioxide-2-carboxylateC17H30O4S90% de[α]D20=-28.7 (c 0.013, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (1R,2S,5R,2′R,3′R)((2R,3R)-Tetrahydro-3-methyl-2H-thiopyran-1,1-dioxide-2-yl)methanolC7H14O3S[α]D20=-16.7 (c 0.005, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2R,3R)Ethyl (2S,3S)-tetrahydro-3-methyl-2H-thiopyran-1,1-dioxide-2-carboxylateC9H16O4S[α]D20=+32.5 (c 0.005, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2S,3S)Ethyl (2R,3S)-tetrahydro-3-methyl-2H-thiopyran-1,1-dioxide-2-carboxylateC9H16O4S[α]D20=-36.8 (c 0.003, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2R,3S)Ethyl 2-((R)-4-(4-toluenesulfonyloxy)pentylsulfonyl)acetateC16H24O7S2[α]D20=+14.1 (c 0.017, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)(R)-1,4-Bis(4-toluenesulfonyloxy)pentaneC19H24O6S2[α]D20=+15.1 (c 0.023, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
Co-reporter:Christian S. Jungong, Jinu P. John, Alexei V. Novikov
Tetrahedron Letters 2009 50(17) pp: 1954-1957
Publication Date(Web):
DOI:10.1016/j.tetlet.2009.02.044
