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Volumn 74, Issue 17, 2009, Pages 6851-6854

Diastereoselective alkylations of a protected cysteinesulfenate

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATING AGENTS; CHEMICAL EQUATIONS; COUNTERIONS; DIASTEREOMERIC RATIOS; DIASTEREOSELECTIVE ALKYLATION; LOW TEMPERATURES; SULFINYL GROUP;

EID: 69549108555     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901021r     Document Type: Article
Times cited : (21)

References (50)
  • 31
    • 69549148750 scopus 로고    scopus 로고
    • note
    • One unoptimized example of this work has been reported previously, see ref 7. Herein we significantly expand upon that contribution, with optimizations, more examples, complete characterizations, and alkylation models.
  • 35
    • 69549142011 scopus 로고    scopus 로고
    • note
    • Full experimental detail including a reaction equation are part of the Supporting Information.
  • 36
    • 69549100878 scopus 로고    scopus 로고
    • note
    • The use of excess base brought about lower yields and increased byproducts including protected dehydroalanine and dibenzyl sulfoxides, when the alkylation was performed with a benzyl bromide.
  • 37
    • 0017783272 scopus 로고
    • To confirm the sulfoxides were kinetic products arising directly from alkylation chemistry, selected sulfoxides were thermolyzed to determine if the observed dr value were caused by (a) selective thermal breakdown of one diasteromer or (b) thermal conversion of one isomer to the other. No evidence in support of either of these processes was observed. See
    • To confirm the sulfoxides were kinetic products arising directly from alkylation chemistry, selected sulfoxides were thermolyzed to determine if the observed dr value were caused by (a) selective thermal breakdown of one diasteromer or (b) thermal conversion of one isomer to the other. No evidence in support of either of these processes was observed. See: Rich, D. H.; Tam, J. P. J. Org. Chem. 1977, 42, 3815-3820.
    • (1977) J. Org. Chem. , vol.42 , pp. 3815-3820
    • Rich, D.H.1    Tam, J.P.2
  • 43
    • 69549129850 scopus 로고    scopus 로고
    • note
    • 3.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.