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Reaction of 1,3‐Disubstituted Acetone Derivatives with Pseudohalides: A Simple Approach to Spiro[4.4]nonane‐Type Bis‐Oxazolidines and ‐Imidazolidines (Bicyclic Carbamates, Thiocarbamates, Ureas, and Thioureas)
Author(s) -
Saul Robert,
Kern Thorsten,
Kopf Jürgen,
Pintér István,
Köll Peter
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(200001)2000:1<205::aid-ejoc205>3.0.co;2-j
Subject(s) - chemistry , bicyclic molecule , thio , organic chemistry , oxazolidine , brucine , cyanamide , diastereomer , thiocarbamate , medicinal chemistry , strychnine , biochemistry
Prochiral 1,3‐dihydroxyacetone forms racemic oxazolidine‐ and oxazoline‐type spiro[4.4]nonanes upon reactions with potassium (thio)cyanate and cyanamide. In contrast, 1,3‐diaminoacetone yields only the corresponding spiro‐bisimidazolidinethione under similar conditions together with monocyclic by‐products, but the spiro‐bisimidazolidinone is accessible by reaction of 1,3‐dichloroacetone with urea. The resolution of the racemic spiro‐bisoxazolidinethione 2a was achieved by using brucine as the resolving agent.