Application of cis-2-amino-3,3-dimethyl-1-indanol as an efficient chiral auxiliary to the asymmetric Ireland-Claisen rearrangement. Improvement of the diastereoselectivity by combinational use of chlorodimethylsilane as a silylating agent

Enantiomer

Volumn 5, Issue 1, 2000, Pages 105-108

  Matsui, Satoshi ^a   Oka, Natsuhisa ^a   Hashimoto, Yukihiko ^a   Saigo, Kazuhiko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Asymmetric Ireland Claisen rearrangement; Chlorodimethylsilane; cis 2 amino 3,3 dimethyl 1 indanol

Indexed keywords

CARBOXYLIC ACID; CHLORODIMETHYLSILANE; CIS 2 AMINO 3,3 DIMETHYL 1 INDANOL; INDAN DERIVATIVE; OXAZOLIDINONE DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; PRIORITY JOURNAL; STEREOCHEMISTRY; TECHNIQUE;

EID: 0034072110     PISSN: 10242430     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (21)

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18. For examples, see: Stereoselective Synthesis, G. Helmchen, R.W. Hoffmann, J Mulzer and E. Schaumann (Eds.). Georg Thieme Verlag: Stuttgart, 1996, Vol. 6, pp. 3412-3419 and references cited therein.
19. The substrates (1R,5S)-3 were prepared as similar to the synthesis of rac-3a shown in Scheme 1: The sodium salt of oxazolidinone (1R,5S)-2, obtained by treatment of (1R,5S)-2[3] with NaH, was allowed to react with the corresponding bromoacetic acid allyl ester derivatives in dimethylformamide at r.t. for 1 h to give (1R,5S)-3 in 90-95% yields.
20. As can be seen from entry 1 in Table II, enantiopure (1R,5S)-3a gave almost the same result as did rac-3a (Table I, entry 1).
21. S. Matsui, N. Oka, Y. Hashimoto and K. Saigo, unpublished results (Fig. 1).