Highly diastereoselective Michael additions onto dienyl bis-sulfoxides

• Published in: Synthesis (Stuttgart) no. 14; pp. 2449 - 2452
• Main Authors: Brebion, F, Goddard, JP, Fensterbank, L, Malacria, M
• Format: Journal Article
• Language: English
• Published: STUTTGART Thieme Medical Publishers 02.09.2005
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; Michael addition; bis-sulfoxide; ASYMMETRIC-SYNTHESIS; cryptophycin; REACTIVITY; vinylcyclopropane; BIS(SULFOXIDES)

An optimized procedure for the preparation of (S-s,S-s)-bis(p-tolylsulfinyl)methane (4) is reported. Condensation of the lithium salt of 4 onto cinnamaldehyde furnished bis-sulfoxide dienyl derivative 5, a remarkable 1,4-Michael acceptor that can lead in a highly diastereoselective manner to vinyley...