Starting from (S)-ethyl lactate and (S)-ethyl mandelate the homochiral hydrazonoyl chlorides 4b-d have been synthesised. Their base treatment promoted the in situ generation of the corresponding nitrilimines 5b-d, which gave the enantiopure title compounds with good overall yields and diastereoselectivities.
Stereoselective intramolecular cycloadditions of homochiral nitrilimines: synthesis of enantiopure (6S)-substituted-2,3,3a,4,5,6-hexahydro-furo[3,4-c]pyrazoles / G. Molteni, L. De Benassuti, L. Garanti. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 15:7(2004), pp. 1127-1131. [10.1016/j.tetasy.2004.02.002]
Stereoselective intramolecular cycloadditions of homochiral nitrilimines: synthesis of enantiopure (6S)-substituted-2,3,3a,4,5,6-hexahydro-furo[3,4-c]pyrazoles
G. Molteni;L. De Benassuti;L. Garanti
2004
Abstract
Starting from (S)-ethyl lactate and (S)-ethyl mandelate the homochiral hydrazonoyl chlorides 4b-d have been synthesised. Their base treatment promoted the in situ generation of the corresponding nitrilimines 5b-d, which gave the enantiopure title compounds with good overall yields and diastereoselectivities.
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