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Rhodium(i)-catalyzed asymmetric hydroboration of alkenes with 1,3,2-benzodioxaborole

โœ Scribed by Makoto Sato; Norio Miyaura; Akira Suzuki

Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
273 KB
Volume
31
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Several rhodium(I) complexes containing chiral phosphine, (+) DIOP, (+> BINAP, (S,S) CHIRAPHOS, and (S)(R) BPPFA, have been found to be effective as catalyst for the asymmetric hydrobomtion of pm&h-al alkenes with catecholborane (1,3,2benzodioxaborole) to give optically active 2-alkyl-1,3,2-benzodioxaboroles. Among the ligands e xarnind, DIOP has been recognized to be most effective to give high asymmetric induction.

Recently, Ndth and Mannigz reported that alkenes and alkynes can be hydroborated with catecholborane (2) in the presence of Rh-catalyst under extremely mild conditions. Although catalytic

๐Ÿ“œ SIMILAR VOLUMES

Asymmetric double hydroboration of 1,3-d
Asymmetric double hydroboration of 1,3-dienes catalyzed by chiral phosphine-rhodium complexes
โœ Yonetatsu Matsumoto; Tamio Hayashi ๐Ÿ“‚ Article ๐Ÿ“… 1991 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 310 KB

Suntnuzry: Reaction of I-phenyl-1,3-butadiene with catecholborane in the presence of a rhodium catalyst bearing ~a~lphosphine ligand such as PPh3 or dppf proceeded regioselectively to give, after oxidation, anti-l-phenyl-1,3-butanediol in a good yield. Use of (R)-BINAP as a chiral ligand for the cat