Chiral Aminated α‐Methylenebenzocycloalkenes from o‐Bromoaryl Aldehydes and Ketones. Issue 12 (7th March 2013)

• Record Type: Journal Article
• Authors: Sirvent, Juan Alberto; Foubelo, Francisco; Yus, Miguel
• Is Part Of: European journal of organic chemistry. Issue 12(2013)
• Page Start: 2461
• Page End: 2471
• Publication Date: 2013-03-07
• Subjects: Fused‐ring systems -- Allylation -- Cyclization -- Diastereoselectivity -- Chiral auxiliaries -- Indium; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201201712
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Chiral tert ‐butylsulfinyl imines3, which are easily prepared from the corresponding bromo carbonyl compounds1 and tert ‐butanesulfinamide (2 ), undergo a diastereoselective allylation by using indium metal and allyl bromide to give the corresponding homoallyl sulfinylamines4 . Treatment of compounds4 with a catalytic amount of palladium acetate and triphenylphosphane gives exo ‐methylene‐substitutedsulfinylamino)benzocycloalkenes5 (five‐ to seven‐membered rings) that are easily deprotected with hydrochloric acid to give chiral primary amines6 . Abstract : Enantioenriched nitrogen‐containing α‐methylenebenzocycloalkenes are prepared through a sequential diastereoselective indium‐promoted allylation of chiral N ‐ tert ‐butylsulfinyl imines and an intramolecular Heck reaction.