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Volumn 44, Issue 18, 2003, Pages 3609-3611

Stereospecific synthesis of chiral tertiary alkyl-aryl ethers via Mitsunobu reaction with complete inversion of configuration

Author keywords

Alkyl aryl ether; Inversion; Mitsunobu reaction; SN2 displacement; Tertiary alcohols

Indexed keywords

ALCOHOL DERIVATIVE; ALKYL ARYL ETHER; PHENOL;

EID: 0037471454     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00728-7     Document Type: Article
Times cited : (64)

References (20)
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    • For intermolecular reactions: (a) Bittner, S.; Assaf, Y. Chem. Ind. (London) 1975, 281; (b) Subramanian, R. S.; Balasubramanian, K. K. Synth. Commun. 1989, 19, 1255; (c) Subramanian, R. S.; Balasubramanian, K. K. Tetrahedron Lett. 1989, 30, 2297; (d) Brunner, H.; Hankofer, P.; Treittinger, B. Chem. Ber. 1990, 1029. For intramolecular reactions: (d) Reisch, J.; Voerste, A. A. W. J. Chem. Soc., Perkin Trans. 1 1994, 3251.
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    • Subramanian, R.S.1    Balasubramanian, K.K.2
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    • (1989) Tetrahedron Lett. , vol.30 , pp. 2297
    • Subramanian, R.S.1    Balasubramanian, K.K.2
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  • 10
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    • For intermolecular reactions: (a) Bittner, S.; Assaf, Y. Chem. Ind. (London) 1975, 281; (b) Subramanian, R. S.; Balasubramanian, K. K. Synth. Commun. 1989, 19, 1255; (c) Subramanian, R. S.; Balasubramanian, K. K. Tetrahedron Lett. 1989, 30, 2297; (d) Brunner, H.; Hankofer, P.; Treittinger, B. Chem. Ber. 1990, 1029. For intramolecular reactions: (d) Reisch, J.; Voerste, A. A. W. J. Chem. Soc., Perkin Trans. 1 1994, 3251.
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    • and references cited therein
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    • (±)-1 was made from alkylation of 4-(benzyloxy)phenol with methyl 2-bromobutyrate followed by α-methylation with methyl iodide and subsequent chiral HPLC separation afforded enantiomerically pure
    • Racemic ether (±)-1 was made from alkylation of 4-(benzyloxy)phenol with methyl 2-bromobutyrate followed by α-methylation with methyl iodide and subsequent chiral HPLC separation afforded enantiomerically pure (R)-1 and (S)-1 (communication with Dr. R. Desai in our laboratories).
  • 14
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    • Attempts to synthesis chiral ether (S)-1 using the Pd-catalyzed cross-coupling of chiral alcohol (S)-2 and 4-(benzyloxy)phenyl bromide were unsuccessful. However, the copper-promoted cross-coupling of (S)-2 with 4-(benzyloxy)phenylboronic acid has afforded a low yield of (S)-1 with compete retention of configuration that was confirmed by chiral HPLC assay (unpublished results of Conlon, D. A.; Drahus, A. L. and Shi, Y.-J. in our laboratories). For the copper-promoted arylation of phenols with arylboronic acid, see: Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937.
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    • Evans, D.A.1    Katz, J.L.2    West, T.R.3
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    • The chiral alcohol. and references cited therein
    • The chiral alcohol (S)-2 is activated by the α-ester moiety, see: Bordwell F.G., Brannen W.T. Jr. J. Am. Chem. Soc. 5:1964;4645. and references cited therein.
    • (1964) J. Am. Chem. Soc. , vol.5 , pp. 4645
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  • 17
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    • For temperature effects on the Mitsunobu reaction, see Ref. 2b
    • For temperature effects on the Mitsunobu reaction, see Ref. 2b.
  • 18
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    • The order of addition of reagents was critical, see Ref. 2b.
    • The order of addition of reagents was critical, see Ref. 2b.
  • 19
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    • (S)-2 (0.76 g, 5.76 mmol) and DIAD (1.40 ml, 7.12 mmol) was made in toluene (4.0 ml) and then slowly added to a mixture of phenol
    • 4), eluent (B): MeCN, gradient (25°C): A/B from 40/60 to 20/80 over 20 min, 1.0 ml/min, 210 nm, retention time: 9.84 min for (R)-1 and 13.38 min for (S)-1 ].
  • 20
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    • 13C) and LCMS.
    • 13C) and LCMS.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.