Enantioselective Addition of a 2‐Alkoxycarbonyl‐1, 3‐dithiane to Imines Catalyzed by a Bis(guanidino)iminophosphorane Organosuperbase. Issue 52 (20th October 2015)

• Record Type: Journal Article
• Authors: Kondoh, Azusa; Oishi, Masafumi; Takeda, Tadahiro; Terada, Masahiro
• Is Part Of: Angewandte Chemie international edition. Volume 54:Issue 52(2015)
• Page Start: 15836
• Page End: 15839
• Publication Date: 2015-10-20
• Subjects: asymmetric catalysis -- 1, 3‐dithianes -- organocatalysis -- organosuperbases -- phosphazenes; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201508178
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A chiral bis(guanidino)iminophosphorane catalyzes enantioselective addition reactions of a 1, 3‐dithiane derivative as a pronucleophile. The chiral uncharged organosuperbase facilitates the addition of benzyloxycarbonyl‐1, 3‐dithiane to aromatic N ‐Boc‐protected imines to provide optically active α‐amino‐1, 3‐dithiane derivatives, which are valuable versatile building blocks in organic synthesis. Abstract : A chiral organosuperbase catalyzes enantioselective addition reactions of a 2‐alkoxycarbonyl‐1, 3‐dithiane. In particular, the chiral uncharged bis(guanidino)iminophosphorane catalyst facilitates their addition to aromatic N‐Boc‐protected imines to provide optically active α‐amino‐1, 3‐dithiane derivatives, which are valuable and versatile building blocks in organic synthesis.