Diastereoselective allylation and crotylation of N-tert-butanesulfinyl imines with allylic alcohols.
نویسندگان
چکیده
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.
منابع مشابه
Diastereoselective allylation and crotylation of N-unsubstituted imines derived from ketones.
A wide variety of tertiary carbinamines are synthesized in high yields via diastereoselective allylation and crotylation of in situ generated N-unsubstituted ketimines.
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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.
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متن کاملHighly diastereoselective construction of acyclic systems with two adjacent quaternary stereocenters by allylation of ketones.
Unsymmetrical ketones and allyltitanocenes generated by the desulfurizative titanation of γ,γ-disubstituted allyl phenyl sulfides react under highly diastereoselective construction of adjacent quaternary stereocenters (see scheme; R(L) = large group, R(S) = small group). The title reaction is stereospecific: the anti- and syn-homoallylic alcohols are obtained by the reaction of E- and Z-allylic...
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ورودعنوان ژورنال:
- Chemical communications
دوره 50 52 شماره
صفحات -
تاریخ انتشار 2014