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Volumn 8, Issue 19, 2002, Pages 4443-4453

Analysis of stereochemical convergence in asymmetric Pd-catalysed allylic alkylation reactions complicated by halide and memory effects

Author keywords

Allylic compounds; Asymmetric catalysis; Memory effects; Palladium; Stereochemical convergence

Indexed keywords

CATALYST ACTIVITY; PALLADIUM; STEREOCHEMISTRY;

EID: 0037020302     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20021004)8:19<4443::AID-CHEM4443>3.0.CO;2-3     Document Type: Article
Times cited : (63)

References (53)
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    • note
    • Matched refers to a favourable configurational relationship of the substrate with the catalyst. The matched substrate will give an ee of product that is closer (or identical) in absolute configuration and magnitude to the intrinsic selectivity of the catalyst as compared to the mismatched. Most often, the matched substrate reacts faster than the mismatched and there will thus be a kinetic resolution process prior to complete reaction.
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    • 1]-1c, confirms that secondary kinetic isotope effects are small (< 1.05/ 1.00) in relation to the memory effects that are of interest and thus the results can be translated directly back to the unlabelled substrate.
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    • Note that it has been observed in some cases that diastereoisomer interconversion is accelerated by nucleophile, for example malonate: J. M. Brown, D. I. Hulmes, P. J. Guiry, Tetrahedron 1994, 50, 4493-4506.
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    • 2H NMR spectroscopy).
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    • a of cyclopentadiene with ROH and the ready prototropy in cyclopentadiene, it is hard to conceive of a stereochemical labelling experiment that would confirm either the location or the stereochemistry of the β-elimination.
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    • For a recent review of some of the effects that halide ions can have on asymmetric transition metal catalysed reactions, including allylic alkylations, see: K. Fagnou, M. Lautens, Angew. Chem. 2002, 114, 26-49; Angew. Chem. Int. Ed. 2002, 41, 26-47.
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    • For a recent review of some of the effects that halide ions can have on asymmetric transition metal catalysed reactions, including allylic alkylations, see: K. Fagnou, M. Lautens, Angew. Chem. 2002, 114, 26-49; Angew. Chem. Int. Ed. 2002, 41, 26-47.
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    • Commercial software (Leipold Associates, USA)
    • Commercial software (Leipold Associates, USA).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.