Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 10, Issue 34, Pages 6876-6884Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2ob26068a
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Funding
- National Natural Science Foundation of China [21072020]
- Science and Technology Innovation Program of Beijing Institute of Technology [2011CX01008]
- Development Program for Distinguished Young and Middle-aged Teachers of Beijing Institute of Technology
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A highly enantio- and diastereoselective sulfa-Michael addition of thioacetic acid to alpha,beta-disubstituted nitroalkenes catalysed by a chiral squaramide organocatalyst has been described. This organocatalytic reaction at an extremely low catalyst loading (0.2 mol%) furnished synthetically useful beta-nitro sulfides in excellent yields with good diastereoselectivities and high enantioselectivities (up to 94 : 6 dr, 95% ee). In addition, the catalytic reaction can be performed on a 10 gram scale, and facile transformation into taurine derivative is also presented.
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