Direct Catalytic Asymmetric Addition of Alkylnitriles to Aldehydes with Designed Nickel–Carbene Complexes. Issue 16 (10th March 2021)

• Record Type: Journal Article
• Authors: Saito, Akira; Adachi, Shinya; Kumagai, Naoya; Shibasaki, Masakatsu
• Is Part Of: Angewandte Chemie international edition. Volume 60:Issue 16(2021)
• Page Start: 8739
• Page End: 8743
• Publication Date: 2021-03-10
• Subjects: aldehydes -- enantioselectivity -- homogeneous catalysis -- nickel -- nitriles; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202016690
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A direct catalytic asymmetric addition of acetonitrile to aldehydes that realizes over 90 % ee is the ultimate challenge in alkylnitrile addition chemistry. Herein, we report achieving high enantioselectivity by the strategic use of a sterically demanding Ni II pincer carbene complex, which afforded highly enantioenriched β‐hydroxynitriles. This highly atom‐economical process paves the way for exploiting inexpensive acetonitrile as a promising C2 building block in a practical synthetic toolbox for asymmetric catalysis. Abstract : A direct catalytic asymmetric addition of acetonitrile to aldehydes with high enantioselectivity is achieved by the strategic use of a sterically demanding Ni II pincer carbene complex. This afforded highly enantioenriched β‐hydroxynitriles.