Asymmetric Michael addition of thiols to beta-nitrostyrenes using a novel phenylpyrrolidine-based urea catalyst

作者：Kawazoe Souichirou^*; Yoshida Kazuki; Shimazaki Yuichi; Oriyama Takeshi

来源：Tetrahedron Letters, 2015, 56(2): 410-413.

DOI：10.1016/j.tetlet.2014.11.116

• Sulfa-Michael addition
• Nitrostyrene
• Urea catalyst
• Benzyl thiol
• 2-Nitro-1-phenylethylsulfides

The catalyst 1-[(3R,4S)-1-benzyl-4-phenyl-pyrrolidin-3-yl]-3-[3,5-bis(trifluoromethyl)phenyl]urea (8) designed based on 1-[(3R)-1-benzylpyrrolidin-3-yl]-3-[3,5-bis(trifluoromethyl)phenyl]thiourea (4) and 1,3-bis[(3R,4S)-1-benzyl-4-phenylpyrrolidin-3-yl]urea (7) exhibited potent catalytic activity for the asymmetric Michael addition of thiols to beta-nitrostyrenes. A mere 2 mol % of the catalyst afforded 2-nitro-1-phenylethylsulfides in high yields of up to 93% ee.

• 出版日期2015-1-8