Selective functionalization of silyl-N-Cbz-1,3-thiazolidines with aldehydes to homologated α-hydroxy thiazolidines and fused oxazolidinones

Synlett

Volumn , Issue 15, 2006, Pages 2439-2443

  Degl'Innocenti, Alessandro ^a   Capperucci, Antonella ^a   Malesci, Irene ^a   Castagnoli, Giulio ^a   Acciai, Miriam ^a   Nocentini, Tiziano ^a   Pollicino, Salvatore ^b  

^a Synthesis and Study of Biologically Active Heterocycles   (Italy)

^b Department of Organic Chemistry 'A Mangini' ^*  (Italy)

Author keywords

Bicyclic compounds; Cyclization; Fluoride ion catalysis; Fused oxazolidinones; Silyl thiazolidines

Indexed keywords

ALDEHYDE DERIVATIVE; ALPHA HYDROXY THIAZOLIDINE DERIVATIVE; FLUORIDE ION; N CBZ 2 TRIMETHYLSILYL 1,3 THIAZOLIDINE; OXAZOLIDINONE DERIVATIVE; THIAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS; TEMPERATURE;

EID: 33749388729     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-949633     Document Type: Article

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27. +], 130 (36), 115 (39), 91 (100), 87 (78), 77 (38).
28. Variable amounts of benzyloxytrimethylsilane were detected in the reactions affording cyclic compounds 3. However, we were unable to detect silylated derivatives of 5 even before work-up, either under TLC or GC/MS conditions.
29. 3): δ = 30.5, 49.4, 68.0, 71.6, 79.0, 125.5, 127.3, 128.2, 128.4, 134.9, 136.0, 150.9.
30. A referee suggested that one equivalent of fluoride is necessary for total reaction with benzaldehydes substituted with an electron-withdrawing group because there may be an ineffective TMS transfer in these cases. In this event a classical nucleophilic reaction involving the complete desilylation by fluoride would operate.