Enantioselective nucleophilic formylation and cyanation of conjugated enones via Michael addition of formaldehyde SAMP-hydrazone

Journal of the American Chemical Society

Volumn 118, Issue 29, 1996, Pages 7002-7003

  Lassaletta, Jose María ^a   Fernández, Rosario ^a   Martín Zamora, Eloísa ^a   Díez, Elena ^a  

^a UNIVERSITY OF SEVILLE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CYANIC ACID; FORMALDEHYDE; HYDRAZONE DERIVATIVE;

ARTICLE; ENANTIOMER; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; STEREOCHEMISTRY;

EID: 0029931674     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9610500     Document Type: Article

References (30)

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15. The only precedent to our knowledge consists of addition of a chiral oxidized dithioacetal derived reagent which, upon a complicated two-step deprotection sequence, gave poor yields and ee's of the desired products: (a) Colombo, L.; Gennari, C.; Resnati, G.; Scolastico, C. Synthesis 1981, 74-76. (b) Colombo, L., Gennari, C; Resnati, G.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1981, 1284-1286.
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19. 4, etc.) were also unsuccessfully tested. The use of trialkylsilyl inflates as promoters for the addition of soft nucleophiles to enones has recently been reported: Kim, S.; Park, J. H. Synlett 1995, 163-164.
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29. 1 should result in a much higher energy for B than for A, according to the absolute configuration and the high induction observed. Such geometries, stabilized by secondary orbital interactions, have been demonstrated to be operative for closely related systems: Pfau, M.; Tomas. A.; Lim, S.; Revial, G. J. Org. Chem. 1995, 60, 1143-1147. equation presented
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