Iridium‐Catalyzed Asymmetric Allyl­ic Substitutions with Bulky ­Amines/Oxidative Double Bond Cleavage – Entry into the Reetz Synthesis of Amino Alcohols. Issue 3 (10th December 2015)

• Record Type: Journal Article
• Authors: Seehafer, Kai; Malakar, Chandi C.; Bender, Markus; Qu, Jianping; Liang, Chen; Helmchen, Günter
• Is Part Of: European journal of organic chemistry. Issue 3(2016)
• Page Start: 493
• Page End: 501
• Publication Date: 2015-12-10
• Subjects: Synthetic methods -- Asymmetric synthesis -- Homogeneous catalysis -- Iridium -- Allylation -- Amination -- Ozonolysis -- Amino alcohols; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201501333
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Branched allylic amines were prepared by Ir‐catalyzed enantioselective allylic aminations with the bulky N‐nucleophiles HN(Boc)2 and HNBn2 . The products were transformed into N ‐protected amino aldehydes, which were either reduced or coupled diastereoselectively with organometallic compounds to give vicinal amino alcohols. A formal synthesis of the neurokinin receptor antagonist (+)‐L‐733060 was carried out as an application. Abstract : Ir‐catalyzed enantioselective allylic aminations with bulky N‐nucleophiles HN(Boc)2 and HNBn2 gave N ‐protected allylic amines, which were transformed into N ‐protected chiral amino aldehydes. These are useful chiral building blocks as previously demonstrated by Reetz et al. A formal synthesis of the neurokinin receptor antagonist (+)‐L‐733060 was carried out as an application.