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Volumn 42, Issue 7, 2003, Pages 787-790

Stereoselective solid-phase synthesis of chiral piperidine derivatives by using an immobilized galactose auxiliary

Author keywords

Carbohydrates; Chiral auxiliaries; Conjugate addition; Nitrogen heterocycles; Solid phase synthesis

Indexed keywords

CONDENSATION; DERIVATIVES; SYNTHESIS (CHEMICAL);

EID: 0037450065     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200390208     Document Type: Article
Times cited : (24)

References (47)
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    • note
    • -1 by direct lithiation of commercially available polystyrene resin (crosslinked with 1% divinylbenzene, 100-200 mesh) with nBuLi and subsequent treatment with dichlorodiisopropylsilane (see also ref. [12]).
  • 27
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    • note
    • This enables the direct analysis of diastereomeric N-galactosylated products and of potential side products and facilitates the analysis of complex reaction sequences on the solid-phase.
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    • The presence of the pivaloyl group at C-2 is necessary for effective diastereofacial differentiation of glycosyl imines (review: K. Rück, H. Kunz, Angew. Chem. 1993, 105, 355-377; Angew. Chem. Int. Ed. Engl. 1993, 32, 336-358); the other hydroxy functions are pivaloyl or pseudopivaloyl (as at C-6 in 4) protected, to increase the stability of the auxiliary against organometallic reagents.
    • (1993) Angew. Chem. , vol.105 , pp. 355-377
    • Rück, K.1    Kunz, H.2
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    • 33748831238 scopus 로고
    • The presence of the pivaloyl group at C-2 is necessary for effective diastereofacial differentiation of glycosyl imines (review: K. Rück, H. Kunz, Angew. Chem. 1993, 105, 355-377; Angew. Chem. Int. Ed. Engl. 1993, 32, 336-358); the other hydroxy functions are pivaloyl or pseudopivaloyl (as at C-6 in 4) protected, to increase the stability of the auxiliary against organometallic reagents.
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 336-358
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    • note
    • The loading capacity was calculated from the nitrogen content of a resin sample that was washed thoroughly and dried for 48 h at 40 °C under high vacuum.
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    • H. Kunz, M. Weymann, M. Follmann, P. Allef, K. Oertel, M. Schultz-Kukula, A. Hofmeister, Pol. J. Chem. 1999, 73, 15-27. N-Carbamoyl-5,6-didehydropiperidin-4-ones and their functionalization have been studied extensively by Comins et al.: D. L. Comins, J. Heterocycl. Chem. 1999, 36, 1491-1500.
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    • note
    • After evaporation of the combined cleavage and washing solutions, the residue was subjected to filtration through a short plug of silica, the crude product was eluted with petroleum ether/ ethyl acetate (1/1), and after removal of the solvent the residue was analyzed by HPLC-MS.


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