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Volumn 129, Issue 30, 2007, Pages 9302-9303

Rhodium-catalyzed enantioselective desymmetrization of meso-3,5-dimethyl glutaric anhydride: A general strategy to syn-deoxypolypropionate synthons

Author keywords

[No Author keywords available]

Indexed keywords

3,5 DIMETHYLGLUTARIC ANHYDRIDE; ACID ANHYDRIDE; DEOXYPOLYPROPIONATE; PROPIONIC ACID DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG;

EID: 34547688944     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja073269s     Document Type: Article
Times cited : (55)

References (42)
  • 21
    • 0037087671 scopus 로고    scopus 로고
    • For asymmetric arylation of glutaric anhydrides using stoichiometric quantities of sparteine, see
    • (c) For asymmetric arylation of glutaric anhydrides using stoichiometric quantities of sparteine, see: Shintani, R.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 1057.
    • (2002) Angew. Chem., Int. Ed , vol.41 , pp. 1057
    • Shintani, R.1    Fu, G.C.2
  • 22
    • 0036353294 scopus 로고    scopus 로고
    • 3,5-Dimethyl glutaric anhydride may be prepared in 35% over three steps: Paquette, L. A.; Boulet, S. L. Synthesis 2002, 888.
    • 3,5-Dimethyl glutaric anhydride may be prepared in 35% over three steps: Paquette, L. A.; Boulet, S. L. Synthesis 2002, 888.
  • 23
    • 33746442416 scopus 로고    scopus 로고
    • For reviews including the asymmetric alcoholysis of cyclic anhydrides, see: a
    • For reviews including the asymmetric alcoholysis of cyclic anhydrides, see: (a) Willis, M. C. J. Chem. Soc., Perkin Trans. 1 1999, 1765.
    • (1999) J. Chem. Soc., Perkin Trans. 1 , pp. 1765
    • Willis, M.C.1
  • 26
    • 34547669136 scopus 로고    scopus 로고
    • Our previously reported Pd-JOSIPHOS system (ref 6a) is not effective with glutaric anhydrides; sp3-nucleophiles are ineffective, while Ph 2Zn adds to 1 in 70% yield and 45% ee; see: Bercot, E. A. Ph.D. Thesis, Colorado State University, 2005
    • 2Zn adds to 1 in 70% yield and 45% ee; see: Bercot, E. A. Ph.D. Thesis, Colorado State University, 2005.
  • 27
    • 0037243669 scopus 로고    scopus 로고
    • For a review of Rh-catalyzed C-C bond forming reactions with organometallic nucleophiles, see: a
    • For a review of Rh-catalyzed C-C bond forming reactions with organometallic nucleophiles, see: (a) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169.
    • (2003) Chem. Rev , vol.103 , pp. 169
    • Fagnou, K.1    Lautens, M.2
  • 29
    • 33748227479 scopus 로고    scopus 로고
    • Phosphinooxazoline references: (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566.
    • Phosphinooxazoline references: (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566.
  • 33
    • 34547680338 scopus 로고    scopus 로고
    • Catalyst loading may be reduced to 2.5 mol, 87, 86% ee, 5 h and 1 mol, 56, 85% ee, 24 h
    • Catalyst loading may be reduced to 2.5 mol % (87%, 86% ee, 5 h) and 1 mol % (56%, 85% ee, 24 h).
  • 34
    • 34547691486 scopus 로고    scopus 로고
    • For catalyst optimization and absolute stereochemistry assignment, see Supporting Information
    • For catalyst optimization and absolute stereochemistry assignment, see Supporting Information.
  • 35
    • 34547662393 scopus 로고    scopus 로고
    • For the majority of substrates, elevated temperatures (50°C) were required for reactivity (e.g., for 2d 25°C, 26% yield, 86% ee; 50°C, 70% yield, 90% ee).
    • For the majority of substrates, elevated temperatures (50°C) were required for reactivity (e.g., for 2d 25°C, 26% yield, 86% ee; 50°C, 70% yield, 90% ee).
  • 36
    • 34547683939 scopus 로고    scopus 로고
    • The reaction proceeds in a cleaner fashion if the Grignard is prepared in situ to avoid byproducts arising from oxidation of the organometallic
    • The reaction proceeds in a cleaner fashion if the Grignard is prepared in situ to avoid byproducts arising from oxidation of the organometallic.
  • 37
    • 34547669135 scopus 로고    scopus 로고
    • Nucleophiles for 2g,h formed by direct Zn-I exchange: Rozema, M. J.; AchyuthaRao, S.; Knochel, P. J. Org. Chem. 1992, 57, 1956.
    • Nucleophiles for 2g,h formed by direct Zn-I exchange: Rozema, M. J.; AchyuthaRao, S.; Knochel, P. J. Org. Chem. 1992, 57, 1956.
  • 39
    • 34547662394 scopus 로고    scopus 로고
    • 7 was isolated as its Bn ester due to the instability of the acid.
    • 7 was isolated as its Bn ester due to the instability of the acid.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.