Copper-catalyzed asymmetric allylation of chiral N-tert-butanesulfinyl imines: dual stereocontrol with nearly perfect diastereoselectivity.
نویسندگان
چکیده
Copper-catalyzed asymmetric allylation of chiral N-tert-butanesulfinyl imines has been described. Dual stereocontrol, through the combination of a chiral auxiliary and a chiral copper complex, has played an important role in achieving the nearly perfect diastereoselectivities (all dr > 99 : 1), especially for ketimine substrates.
منابع مشابه
Diastereoselective allylation and crotylation of N-tert-butanesulfinyl imines with allylic alcohols.
The palladium-catalyzed allylation of N-tert-butanesulfinyl imines with allylic alcohols in the presence of InI as reducing reagent takes place with high diastereoselectivity in reasonable yields. The reaction with crotyl alcohol is totally regioselective, leading to the anti-diastereomer as the main reaction product.
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The diastereoselective addition of an allylic indium intermediate to chiral o-bromophenyl sulfinyl imine 4 proceeded with good levels of diastereoselectivity. The resulting homoallylic amine derivatives were transformed into lactams 7 and 12, which upon copper-mediated intramolecular N-arylation led to the formation of benzo-fused 1-azabicyclo[j.k.0]alkanes 8 and 13. Benzo-fused 2-allyl-substit...
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ورودعنوان ژورنال:
- Organic & biomolecular chemistry
دوره 13 14 شماره
صفحات -
تاریخ انتشار 2015