Anti- and syn-selective cyanosilylation reactions promoted by a sugar-based bifunctional catalyst: Stereoselective syntheses of essential building blocks for HIV protease inhibitors and bestatin

Synlett

Volumn , Issue 5, 2001, Pages 617-620

  Manickam, Govindaswamy ^a   Nogami, Hiroyuki ^a   Kanai, Motomu ^a   Gröger, Harald ^b   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b SKW Trostberg AG   (Germany)

Author keywords

Amino aldehyde; Bestatin; Bifunctional catalyst; Cyanosilylation; HIV protease inhibitors

Indexed keywords

AMINOALDEHYDE; AMPRENAVIR; ANTINEOPLASTIC AGENT; BESTATIN; KYNOSTATIN 272; PHENYLALANINE; PROTEINASE INHIBITOR;

ARTICLE; CATALYST; CHEMICAL REACTION; DIASTEREOISOMER; DRUG STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0035031244     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2001-13383     Document Type: Article

References (34)

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29. The initial reaction rate of 10 was 1.2 times faster than 16, when 9 mol% of 6 was used. Considering that 10 gave a slightly higher diastereoselectivity than 16, the combination of 6 and 10 appeared to be the matched pair.
30. 2AlCl, only 35% yield of 13 was obtained after 48 h with lower diastereomeric ratio (13a:13s) of 78:22.
31. The silylated ligand of catalyst 7 gradually appeared on TLC, indicating partial decomposition of the catalyst under the reaction conditions. However, even a trace amount of the silylated ligand of 6 was not observed. The reason why catalyst 6 is more stable than 7 is currently under investigation.
32. The matched transition state as 28 in the combination of 6 and 16 might have some contribution, although the relative position of the aldehyde and the activated TMSCN seems not optimum. Formula represented
33. 2O gave 3.2 g of pure 29 (75% yield).
34. 2, MeOH.