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Volumn 38, Issue 38, 1997, Pages 6631-6634

Design and implementation of new auxiliaries for asymmetric enolate alkylations

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; HETEROCYCLIC COMPOUND;

EID: 0030815182     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01576-1     Document Type: Article
Times cited : (3)

References (14)
  • 1
    • 0003643894 scopus 로고
    • For reviews of auxiliary-mediated asymmetric alkylations, see: (a) J. Wiley & Sons: New York, NY
    • For reviews of auxiliary-mediated asymmetric alkylations, see: (a) Seyden-Penne, J.; Chiral Auxiliaries and Ligands in Asymmetric Synthesis; J. Wiley & Sons: New York, NY, 1995; pp 172-187.
    • (1995) Chiral Auxiliaries and Ligands in Asymmetric Synthesis , pp. 172-187
    • Seyden-Penne, J.1
  • 3
    • 0001594845 scopus 로고
    • For examples of asymmetric auxiliaries, see: (c)
    • For examples of asymmetric auxiliaries, see: (c) Evans, D.A.; Mather, D.J.; Innis, M.D. J. Am. Chem. Soc. 1985, 107, 4346-4348.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 4346-4348
    • Evans, D.A.1    Mather, D.J.2    Innis, M.D.3
  • 4
  • 8
    • 0029066475 scopus 로고
    • For a review of pi-stacking in stereoselective synthesis, see
    • For a review of pi-stacking in stereoselective synthesis, see: Jones, G.B.; Chapman, B.J. Synthesis 1995, 475-497.
    • (1995) Synthesis , pp. 475-497
    • Jones, G.B.1    Chapman, B.J.2
  • 9
    • 0342729562 scopus 로고    scopus 로고
    • HPLC conditions are as follows with 15% EtOAc in hexanes; (a) Semi-preparative: 12 mL/min on a Rainin Silica 25 cm × 21.4 mm, 5 μm 100 Å column. (b) Analytical: 0.75 mL/min on a Rainin Silica 25 cm × 4.6 mm, 5 μm 100 Å column
    • HPLC conditions are as follows with 15% EtOAc in hexanes; (a) Semi-preparative: 12 mL/min on a Rainin Silica 25 cm × 21.4 mm, 5 μm 100 Å column. (b) Analytical: 0.75 mL/min on a Rainin Silica 25 cm × 4.6 mm, 5 μm 100 Å column.
  • 10
    • 0343599489 scopus 로고    scopus 로고
    • note
    • 3. 6a: δ 7.64 (br s, 1H), 7.26 (m, 5H), 6.83 (s, 1H), 5.33 (d, J = 7.5 Hz, 1H), 4.32 (d, J = 16.2 Hz, 1H), 4.10 (d, J = 16.2 Hz, 1H), 3.83 (s, 3H), 0.92 (s, 9H). 6b: δ 7.56 (br s, 1H), 7.25 (m, 5H), 6.69 (s, 1H), 5.13 (d, J = 7.8 Hz, 1H), 4.97 (q, J = 6.9 Hz, 1H), 3.84 (s, 3H), 1.52 (d, J = 6.6 Hz, 3H), 0.95 (s, 9H). 6c: δ 7.65 (br s, 1H), 7.43 (d, J = 7.2 Hz, 1H) 7.27 (m, 4H), 6.62 (s, 1H), 5.33 (d, J = 4.5 Hz, 1H), 4.79 (q, J = 6.9 Hz, 1H), 3.89 (s, 3H), 1.45 (d, J = 6.9 Hz, 3H), 0.80 (s, 9H). 7a: δ 7.72 (br s, 1H), 7.26 (m, 8H), 7.03 (m, 3H), 5.40 (d, J = 7.8 Hz, 1H), 4.36 (d, J = 16.2 Hz, 1H), 4.14 (d, J = 16.2 Hz, 1H), 3.88 (s, 3H), 2.55 (s, 2H), 0.80 (s, 3H), 0.79 (s, 3H). 7b: δ 7.52 (br s, 1H), 7.26 (m, 5H), 7.08 (m, 2H), 6.84 (s, 1H), 5.17 (d, J = 7.8 Hz, 1H), 4.99 (q, J = 7.2 Hz, 1H), 3.86 (s, 3H), 2.59 (m, 2H), 1.53 (d, J = 6.9 Hz, 3H), 0.82 (s, 9H). 7c: δ 7.69 (br s, 1H), 7.46 (m, 2H) 7.3-7.0 (m, 7H), 6.90 (m, 2H), 5.39 (d, J = 7.5 Hz, 1H), 4.87 (q, J = 6.9 Hz, 1H), 3.90 (s, 3H), 2.41 (m, 2H), 1.48 (d, J = 6.9 Hz, 3H), 0.70 (s, 3H), 0.61 (s, 3H). 8a: δ 8.0-7.7 (m, 3H), 7.5-7.2 (m, 11H), 5.44 (d, J = 7.8 Hz, 1H), 4.42 (d, J = 16.2 Hz, 1H), 4.17 (d, J = 16.2 Hz, 1H), 3.91 (s, 3H), 3.08 (m, 2H), 0.83 (s, 3H), 0.80 (s, 3H. 8b: δ 8.02 (d, J = 8.1 Hz, 1H), 7.9-7.7 (m, 2H), 7.6-7.2 (m, 10H), 7.00 (s, 1H), 5.22 (d, J = 7.8 Hz, 1H), 5.02 (q, J = 6.9 Hz, 1H), 3.89 (s, 3H), 3.13 (m, 2H), 1.57 (d, J = 7.2 Hz, 3H), 0.84 (s, 3H), 0.83 (s, 3H. 8c: δ 7.8-7.0 (m, 14H), 5.41 (d, J = 7.8 Hz, 1H), 4.89 (q, J = 6.9 Hz, 1H), 3.94 (s, 3H), 2.93 (m, 2H), 1.51 (d, J = 6.9 Hz, 3H), 0.74 (s, 3H), 0.62 (s, 3H).
  • 12
    • 0342729560 scopus 로고    scopus 로고
    • Chiral HPLC conditions as follows: 98/2/0.05 hexanes/isopropanol/acetic acid at 1 mL/min; Pirkle Whelk-O 1, 25 cm × 4.6 mm, 5 μm 100 Å column on a Hewlett Packard Series 1050 with diode array detector
    • Chiral HPLC conditions as follows: 98/2/0.05 hexanes/isopropanol/acetic acid at 1 mL/min; Pirkle Whelk-O 1, 25 cm × 4.6 mm, 5 μm 100 Å column on a Hewlett Packard Series 1050 with diode array detector.
  • 13
    • 0342294517 scopus 로고    scopus 로고
    • The HPLC signal of the minor diastereomer (8c) was obscured by minor impurities. The reported ratio is a minimum value for the selectivity
    • The HPLC signal of the minor diastereomer (8c) was obscured by minor impurities. The reported ratio is a minimum value for the selectivity.


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