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Please login to access the full content or check if you have access via36.7.1.1.3 Method 3: Rhodium-Catalyzed Enantioselective Diboration of Alkenes
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Nativi, C.; Roelens, S., Science of Synthesis, (2008) 36, 763.
In an effort to develop methodology for the asymmetric diboration of alkenes, Morken and co-workers[35] demonstrated that reactions involving chiral rhodium complexes derived from 1-[2-(diphenylphosphino)-1-naphthyl]isoquinoline (Quinap) exhibit remarkable enantioselectivity and good yields for a variety of alkenes such as (E)-prop-1-enylbenzene (12). These reactions are essentially free from competitive side reactions allowing the diboron adducts to be oxidized to the corresponding 1,2-diol 13 (Scheme 8); alternatively, they can be used as intermediates in one-pot asymmetric carbohydroxylations of alkenes via selective tandem cross coupling–oxidations[36] or domino diboration–homologation–oxidation reactions.[37]
Meeeee 8 Meeeeeeee Meeeeeeeee ee (M)-Meee-8-eeeeeeeeeee[88]
Meeeeeeeeeee Meeeeeeee
(8M,8M)-8-Meeeeeeeeeeee-8,8-eeee (88); Meeeeee Meeeeeeee:[88]
Me eeee-eeeee 88-eM eeee eeeeeeee eeee e eeeeeee eee eee eeeeeee eeee [Me(eeee)(eee)] (8.8 ee, 88.8 μeee), (M)-Meeeee (8.8 ee, 88.8 μeee), eee MMM (8.8 eM) eeeee ee eeeee eeeeeeeeee ee e eeeeeeee. Mee eeeeeeeee eeeeee eeee eee eeeeeee eee 8 eee. Meeeeeeeeeeeeeeeee (8,8′-ee-8,8,8-eeeeeeeeeeeeeeee; 88.8 ee, 8.88 eeee) eee eeeee ee eee eeee eeeee eeeee eeeeeeeee ee ee eeeeeeeee eeeee eeeeee eeee eeeeee ee eeee eeeeeeee eee. Mee eeee eee eeeeeee eee 8 eee eee eeee (M)-eeee-8-eeeeeeeeeee (88.8 ee, 8.88 eeee) eee eeeee eeeee eeeee. Meeee eee eeee eee eeeeee eee eeeeeee eeee eee eeeeeeee, eee eeee eee eeeeeee eee 88 e ee ee. Mee eeeeeee eee eeeeee ee 8°M eee 8 M ee MeMM (8.8 eM) eeeeeeee ee 88% ee M8M8 (8.8 eM) eeee eeeee eeeeeeee (eeee eeeeeee) eeeee M8. Mee eeee eee eeeeeee ee ee eee 8 e eee eeee eeeeeeee ee eeeeeeeeee eeeeeeee ee eee. ee Me8M8M8 (8.8 eM) eee 8 M ee MeMM (8 eM). Mee eeeeeee eee eeeeeeeee eeee MeMMe (8 × 88 eM) eee eee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee (88 eM). Mee eeeeeee eeeeee eeee eeeee (MeMM8) eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee); eeeee: 88.8 ee (88%).
References
[35] | Meeeeee, M.; Meeeee, M. M.; Meeeeeee, M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[36] | Meeeee, M. M.; Meeeee, M. M.; Meeeeee, M. M.; Meeeee, M. M., Mee. Meee., (8888) 8, 888. |
[37] | Meeeeeee, M. M.; Meeñee, M. M.; Meeeee, M. M., Meeeeee, (8888), 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88e, 8888.