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Volumn 119, Issue 48, 1997, Pages 11561-11570

A mechanistic and structural investigation of the (-)-sparteine mediated asymmetric benzylic lithiation substitution reactions of N-Boc-N-(p-methoxyphenyl)benzylamine

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLAMINE DERIVATIVE;

EID: 0031468512     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja972225o     Document Type: Article
Times cited : (109)

References (40)
  • 18
    • 17344373383 scopus 로고    scopus 로고
    • 7
    • 7
  • 25
    • 33748633427 scopus 로고
    • This unusual behavior has recently been concluded to arise from a simultaneous increase in s-character and decrease in lithium-carbon covalency. Lambert, C.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1129.
    • (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 1129
    • Lambert, C.1    Schleyer, P.V.R.2
  • 31
    • 17344367427 scopus 로고    scopus 로고
    • 1) was obtained in 78% yield with a 92:8 er
    • 1) was obtained in 78% yield with a 92:8 er.
  • 34
    • 17344368508 scopus 로고    scopus 로고
    • The loss of enantioenrichment and low conversion in toluene was improved by using ether as the solvent to give (R)-12 in 81% yield and 97:3 er
    • The loss of enantioenrichment and low conversion in toluene was improved by using ether as the solvent to give (R)-12 in 81% yield and 97:3 er.
  • 35
    • 17344363228 scopus 로고    scopus 로고
    • note
    • 2 proceeding through an invertive pathway.
  • 36
    • 0001229447 scopus 로고
    • For examples of both invertive and retentive electrophilic trapping of organolithium intermediates, see: (a) Thayumanavan, S.; Lee, S.; Liu, C.; Beak, P. J. Am. Chem. Soc. 1994, 116, 9755. (b) Derwig, C.; Hoppe, D. Synthesis 1996, 149. (c) Gawley, R. E.; Zhang, Q. J. Org. Chem. 1995, 60, 5763.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 9755
    • Thayumanavan, S.1    Lee, S.2    Liu, C.3    Beak, P.4
  • 37
    • 0030069953 scopus 로고    scopus 로고
    • For examples of both invertive and retentive electrophilic trapping of organolithium intermediates, see: (a) Thayumanavan, S.; Lee, S.; Liu, C.; Beak, P. J. Am. Chem. Soc. 1994, 116, 9755. (b) Derwig, C.; Hoppe, D. Synthesis 1996, 149. (c) Gawley, R. E.; Zhang, Q. J. Org. Chem. 1995, 60, 5763.
    • (1996) Synthesis , pp. 149
    • Derwig, C.1    Hoppe, D.2
  • 38
    • 0000190380 scopus 로고
    • For examples of both invertive and retentive electrophilic trapping of organolithium intermediates, see: (a) Thayumanavan, S.; Lee, S.; Liu, C.; Beak, P. J. Am. Chem. Soc. 1994, 116, 9755. (b) Derwig, C.; Hoppe, D. Synthesis 1996, 149. (c) Gawley, R. E.; Zhang, Q. J. Org. Chem. 1995, 60, 5763.
    • (1995) J. Org. Chem. , vol.60 , pp. 5763
    • Gawley, R.E.1    Zhang, Q.2
  • 40
    • 17344370324 scopus 로고    scopus 로고
    • For the reaction with MeOD, we suggest that complexation with (R)-2/6 and (S)-9/TMEDA occurs prior to deuterium transfer
    • For the reaction with MeOD, we suggest that complexation with (R)-2/6 and (S)-9/TMEDA occurs prior to deuterium transfer.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.