Enantioselectivity of the Transfer of Hydrogen Atoms to Acyclic Prochiral Carbon-Centred Radicals Using Chiral Tin Hydrides

✍ Scribed by Kay Schwarzkopf; Michael Blumenstein; Ahlke Hayen; Jürgen O. Metzger

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 441 KB
• Volume: 1998
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199801)1998:1<177::aid-ejoc177>3.0.co;2-z

✦ Synopsis

Racemic α-bromo esters 2 have been reduced via prochiral that the minor diastereomer of tin hydrides 1a and 1b reacts with good enantioselectivity whereas the major diastereomer radicals 5 with low to moderate enantioselectivities using chiral tin hydrides 1 with a stereogenic tin atom containing reacts almost unselectively. The observed enantioselectivities are also strongly influenced by steric effects of the substitu-chiral 2-[(1-dimethylaminoalkyl)phenyl] ligands. The tin hydrides 1 were mixtures of diastereomers. It could be shown ents attached to the radical centre.