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One pot diastereoselective synthesis of new chiral spiro‐1,3,4‐thiadiazoles and 1,4,2‐oxathiazoles from (1 R )‐thiocamphor
Author(s) -
Feddouli Amal,
Itto Moulay Youssef Ait,
Hasnaoui Aïssa,
Villemin Didier,
Jaffrès PaulAlain,
Santos Jana SopkovaDe Oliveira,
Riahi Abdelkhalek,
Huet FranÇOis,
Daran JeanClaude
Publication year - 2004
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570410513
Subject(s) - chemistry , diastereomer , nitrile , thiadiazoles , cycloaddition , absolute configuration , stereochemistry , asymmetric carbon , 1,3 dipolar cycloaddition , chiral auxiliary , medicinal chemistry , organic chemistry , enantioselective synthesis , catalysis , optically active
Herein we report an efficient one pot synthesis of new chiral 4,5‐dihydro‐4‐arylspiro[1,3,4‐thiadiazole]‐5,2′‐camphane‐2‐carboxylic acid ethyl esters 5–7 and 4,5‐dihydro‐3‐arylspiro[1,4,2‐oxathiazole]‐5,2′‐camphane 11–13 , using 1,3‐dipolar cycloaddition of nitrilimines 2–4 and nitrile oxides 8–10 to (1 R )‐thiocamphor 1 respectively. The structure of the newly prepared 1,3,4‐thiadiazoles 5–7 (obtained as pure diastereoisomers) were fully established via spectroscopic analysis and X‐ray structural analysis which proved the absolute configuration of the C5 spiranic carbon to be ( R ). NMR spectral analysis were also very useful to show the new 1,4,2‐oxathiazoles 11–13 are mixtures of two (5 R )/(5 S ) diastereoisomers with the ratio 6:4,7:3 and 6:4 respectively.