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A New Synthesis of (2 S ,3 R ,4 R )‐2‐(Hydroxymethyl)pyrrolidine‐3,4‐diol
Author(s) -
Meng Qingchang,
Hesse Manfred
Publication year - 1991
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19910740222
Subject(s) - chemistry , pyrrolidine , mitsunobu reaction , hydroxymethyl , yield (engineering) , amide , diol , alkylation , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , materials science , metallurgy
The title compound 6 was synthesized from 2,3,5‐tri‐ O ‐benzyl‐ D ‐arabinofuranose ( 7 ) in three steps and 48% overall yield. Moreover, it was shown, in the case of γ‐hydroxy amide 9 , that the Mitsunobu reaction is not suitable for the preparation of γ‐lactams, because O ‐alkylation is predominant.