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Volumn 39, Issue 12, 2000, Pages 2127-2129

A transition state for the enantioselective deprotonation of N-Boc- pyrrolidine with isopropyllithium/(-)-sparteine

Author keywords

Ab initio calculations; Carbanions; Lithium; Transition states

Indexed keywords

ORGANOLITHIUM COMPOUND; PYRROLIDINE DERIVATIVE; SPARTEINE;

EID: 0034674249     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000616)39:12<2127::AID-ANIE2127>3.0.CO;2-H     Document Type: Article
Times cited : (45)

References (26)
  • 2
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    • a) D. Hoppe, F. Hintze, P. Tebben, Angew. Chem. 1990, 102, 1457-1458; Angew. Chem. Int. Ed. Engl. 1990, 29, 1422-1423;
    • (1990) Angew. Chem. Int. Ed. Engl. , vol.29 , pp. 1422-1423
  • 4
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    • b) J. Schwerdtfeger, D. Hoppe, Angew. Chem. 1992, 104, 1547; Angew. Chem. Int. Ed. Engl. 1992, 31, 1505;
    • (1992) Angew. Chem. Int. Ed. Engl. , vol.31 , pp. 1505
  • 10
    • 0000854142 scopus 로고    scopus 로고
    • For reviews, see: a) D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376-2410; Angew. Chem. Int. Ed. Engl. 1997, 36, 2283-2316;
    • (1997) Angew. Chem. , vol.109 , pp. 2376-2410
    • Hoppe, D.1    Hense, T.2
  • 11
    • 0000129326 scopus 로고    scopus 로고
    • For reviews, see: a) D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376-2410; Angew. Chem. Int. Ed. Engl. 1997, 36, 2283-2316;
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 2283-2316
  • 13
    • 33749124991 scopus 로고    scopus 로고
    • Semiempirical PM3 calculations probing diastereoselectivity in the deprotonation of chiral alkyl carbamates have been reported: see, J. Haller, T. Hense, D. Hoppe, Liebigs Ann. 1996, 489-499.
    • (1996) Liebigs Ann. , pp. 489-499
    • Haller, J.1    Hense, T.2    Hoppe, D.3
  • 17
    • 0343347564 scopus 로고    scopus 로고
    • note
    • 2·(-)-sparteine] but this structure clearly need not be maintained in the deprotonation of 2.
  • 21
    • 0343347563 scopus 로고    scopus 로고
    • note
    • Detailed structural data may be found in the Supporting Information.
  • 24
    • 0342478061 scopus 로고    scopus 로고
    • note
    • Structures were constructed, examined, and adjusted prior to geometry optimization using Gaussview. The structures of the other three initial complexes were also modified by rotation about single bonds in order to move the bound iPrLi closer to the α-carbon of the pyrrolidine ring; geometry optimization for these structures did not lead to species with energies lower than those found for 3 or 4.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.