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Volumn 48, Issue 25, 2009, Pages 4634-4638

Enantiospecific synthesis and allylation of all-carbon-substituted a-chiral allylic stannanes

Author keywords

Allylation; Allylic substitution; Enantiospecificity; Stannanes; Stereoselective synthesis

Indexed keywords

ALLYLATION; ALLYLIC SUBSTITUTION; ENANTIOSPECIFICITY; STANNANES; STEREOSELECTIVE SYNTHESIS;

EID: 70349939395     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200901384     Document Type: Article
Times cited : (29)

References (42)
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    • To the best of our knowledge, only a single study on the deliberate preparation of Z-configured a-chiral allylic stannanes has been reported: S. Okamoto, S.-i. Matsuda, D. K. An, F. Sato, Tetrahedron Lett. 2001, 42, 6323-6326.
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    • Tin-based zinc reagents have been employed in 1,2-additions to aldehydes: a S. Mohapatra, A. Bandyopadhyay, D. K. Barma, J. H. Capdevila, J. R. Falck, Org. Lett. 2003, 5, 4759-4762;
    • Tin-based zinc reagents have been employed in 1,2-additions to aldehydes: a) S. Mohapatra, A. Bandyopadhyay, D. K. Barma, J. H. Capdevila, J. R. Falck, Org. Lett. 2003, 5, 4759-4762;
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    • Although triorganostannyl lithium compounds are already relatively soft, in contrast to the related hard triorganosilyl lithium reagents, it is necessary to form the corresponding zinc compounds to enable the allylic substitution of benzoates and acetates without deacylation
    • Although triorganostannyl lithium compounds are already relatively soft, in contrast to the related hard triorganosilyl lithium reagents, it is necessary to form the corresponding zinc compounds to enable the allylic substitution of benzoates and acetates without deacylation.
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    • Reductive metalation and lithium-to-zinc transmetalation release substantial amounts of lithium chloride and zinc chloride. Removal of these Lewis acids by repeated extraction with H2O might be advantageous see the Supporting Information
    • 2O might be advantageous (see the Supporting Information).
  • 36
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    • The relative configuration was determined unequivocally for both diastereomers following a reductive ozonolyis and acetal-ization see the Supporting Information
    • The relative configuration was determined unequivocally for both diastereomers following a reductive ozonolyis and acetal-ization (see the Supporting Information).
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.