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- W2107563441 abstract "(1′S)-(1a; R = Me) [130973-57-8] C8H9NO2S (MW 183.25) InChI = 1S/C8H9NO2S/c1-6-7-4-2-3-5-8(7)12(10,11)9-6/h2-6,9H,1H3/t6-/m0/s1 InChIKey = WZOKMILQIPCVQJ-LURJTMIESA-N (1′R)-(1a) [130973-53-4] C11H15NO2S (MW 225.34) InChI = 1S/C8H9NO2S/c1-6-7-4-2-3-5-8(7)12(10,11)9-6/h2-6,9H,1H3/t6-/m1/s1 InChIKey = WZOKMILQIPCVQJ-ZCFIWIBFSA-N (1′S)-(1b; R = t-Bu) [137694-01-0] InChI = 1S/C11H15NO2S/c1-11(2,3)10-8-6-4-5-7-9(8)15(13,14)12-10/h4-7,10,12H,1-3H3/t10-/m1/s1 InChIKey = OHTMJLXKKSHARP-SNVBAGLBSA-N (1′R)-(1b) [137694-00-9] InChI = 1S/C11H15NO2S/c1-11(2,3)10-8-6-4-5-7-9(8)15(13,14)12-10/h4-7,10,12H,1-3H3/t10-/m0/s1 InChIKey = OHTMJLXKKSHARP-JTQLQIEISA-N (chiral auxiliary: N-enoyl derivatives undergo highly stereoselective Diels–Alder reactions with cyclopentadiene2 and 1,3-dipolar cycloadditions with nitrile oxides;3 enolates of N-acyl derivatives participate in highly stereoselective alkylations, acylations, and aldolizations4) Physical Data: (1a) mp 92 °C. (1′S)-(1a) [α]D20 −30.0° (c 1.21, CHCl3). (1′R)-(1a) [α]D20 +31.0° (c 0.6, EtOH). (1b) mp 129–130 °C. (1′S)-(1b) [α]D20 −53.9° (c 1.00, CHCl3). (1b) has been incorrectly assigned.3 Preparative Methods: both enantiomers of the α-methyl sultam may be prepared on a multigram scale in optically pure form by asymmetric hydrogenation of imine (2a) followed by simple crystallization (eq 1).5 The (R)-enantiomer of the α-t-butyl sultam may also be prepared in enantiomerically pure form by asymmetric reduction of imine (2b) followed by fractional crystallization.3 However, multigram quantities of either enantiomer of the α-t-butyl sultam may be prepared by derivatization of the racemic auxiliary (obtained in 98% yield from reaction of (2b) with Sodium Borohydride in MeOH) with 10‐Camphorsulfonyl Chloride, separation of the resulting diastereomers by fractional crystallization, and acidolysis.3 Prochiral imines (2a) and (2b) are readily prepared from inexpensive Saccharine by treatment with Methyllithium (73%) and t‐Butyllithium (66%), respectively. (1) Handling, Storage, and Precautions: these auxiliaries are white crystalline solids which are stable indefinitely at ambient temperature in sealed containers." @default.
- W2107563441 created "2016-06-24" @default.
- W2107563441 creator A5025860787 @default.
- W2107563441 date "2001-04-15" @default.
- W2107563441 modified "2023-09-28" @default.
- W2107563441 title "α-Methyltoluene-2,α-sultam" @default.
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- W2107563441 doi "https://doi.org/10.1002/047084289x.rm257m" @default.
- W2107563441 hasPublicationYear "2001" @default.
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