Tetrahedron Letters p. 4137 - 4140 (1985)
Update date:2022-08-10
Topics:
Hirama, Masahiro
Shigemoto, Takeo
Ito, Sho
Contrary to the precedents, 1,3-anti stereoselection was found in the intramolecular Michael addition of ethyl threo-5-carbamoyloxy-4-trialkylsilyloxy-2-hexenoate to culminate in a synthesis of N-benzoyl-D,L-daunosamine.The antiperiplanar effect due to the group at 4-position was revealed to play a major role in the stereoselection in this type of reactions.N-benzoyl-D,L-3-epidaunosamine was also synthesized by 1,2-syn asymmetric induction.
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