Copper-catalyzed highly enantioselective synthesis of cyclic allylic and homoallylic alcohols with dialkylzinc reagents

Synthesis

Volumn , Issue 2, 2005, Pages 334-337

  Pineschi, Mauro ^a   Del Moro, Federica ^a   Crotti, Paolo ^a   Di Bussolo, Valeria ^a   Macchia, Franco ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

Asymmetric catalysis; Copper; Desymmetrization; Kinetic resolution; Organozinc reagents

Indexed keywords

ADDITION REACTIONS; CATALYSIS; COPPER; PHOSPHORS; REACTION KINETICS; SYNTHESIS (CHEMICAL); ZINC COMPOUNDS;

DIALKYLZINC REAGENTS; ENANTIOSELECTIVE SYNTHESIS; HOMOALLYLIC ALCOHOLS; MESO ALLYLIC EPOXIDES;

ALCOHOLS;

ALLYL ALCOHOL; COPPER; EPOXIDE; PHOSPHOROAMIDITE; PHOSPHORUS; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 13844270635     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-834864     Document Type: Article

References (20)

1. For a recent overview of the copper-catalyzed ring opening reactions of small-ring heterocycles with dialkylzinc reagents, see: Pineschi, M. New. J. Chem. 2004, 657.
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3. (b) Chiral ligand 1 was recently used in the iridium-catalyzed allylic etherification and amination of achiral allylic esters: Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164.
4. (c) Also see: Lopez, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426.
5. (S,R,R)-Diastereoisomeric phosphoramidite, derived from (S)-BINOL and (R)-bis-phenylethylamine developed by Feringa et al. is to date one of the most effective chiral ligand for several copper-catalyzed enantioselective conjugate additions. For some recent examples, see: (a) Pineschi, M.; Del Moro, F.; Gini, F.; Minnaard, A. J.; Feringa, B. L. Chem. Commun. 2004, 1244.
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19. Pineschi, M.; Del Moro, F.; Crotti, P.; Di Bussolo, V.; Macchia, F. J. Org. Chem. 2004, 69, 2099 and references therein.
20. In this case, the use of lower amounts of the chiral catalyst (<1.0 mol%) gave a very sluggish reaction.