Reformatsky-type reaction of chiral nonracemic α-bromo-α′ -sulfinyl ketones with aldehydes. Synthesis of enantiomerically pure 2-methyl-1,3-diol moieties

Organic Letters

Volumn 5, Issue 5, 2003, Pages 629-632

  Obringer, Michel ^a   Colobert, Françoise ^a   Neugnot, Benjamin ^a   Solladié, Guy ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALDEHYDE DERIVATIVE; KETONE; KETONE DERIVATIVE;

ADDITION REACTION; ARTICLE; CHIRALITY; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; QUANTUM YIELD; REACTION ANALYSIS; REFORMATSKY REACTION; STEREOCHEMISTRY;

EID: 0141563506     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027223+     Document Type: Article

References (35)

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30. 11a-d we noticed that the nonequivalence of the methylene hydrogens α to the sulfoxide group is quite different in the two diastereomers: in the [(R),S(R)]-configuration the Δv value between these two hydrogens is around 40 Hz (in 13, Δv = 50 Hz) and around 80 Hz in the [(S),S(R)]-epimers (in 12 Δv = 79 Hz). (a) Colobert, F.; Des Mazery, R.; Solladié, G.; Carreno, M. C. Org. Lett. 2002, 4, 1723. (b) Solladié, G.; Gressot, L.; Colobert, F. Eur. J. Org. Chem. 2000, 357. (c) Solladié, G.; Adamy, M.; Colobert, F. J. Org. Chem. 1996, 61, 4369. (d) Solladié, G.; Colobert, F.; Denni, D. Tetrahedron: Asymmetry 1998, 9, 3081.
31. 11a-d we noticed that the nonequivalence of the methylene hydrogens α to the sulfoxide group is quite different in the two diastereomers: in the [(R),S(R)]-configuration the Δv value between these two hydrogens is around 40 Hz (in 13, Δv = 50 Hz) and around 80 Hz in the [(S),S(R)]-epimers (in 12 Δv = 79 Hz). (a) Colobert, F.; Des Mazery, R.; Solladié, G.; Carreno, M. C. Org. Lett. 2002, 4, 1723. (b) Solladié, G.; Gressot, L.; Colobert, F. Eur. J. Org. Chem. 2000, 357. (c) Solladié, G.; Adamy, M.; Colobert, F. J. Org. Chem. 1996, 61, 4369. (d) Solladié, G.; Colobert, F.; Denni, D. Tetrahedron: Asymmetry 1998, 9, 3081.
32. 11a-d we noticed that the nonequivalence of the methylene hydrogens α to the sulfoxide group is quite different in the two diastereomers: in the [(R),S(R)]-configuration the Δv value between these two hydrogens is around 40 Hz (in 13, Δv = 50 Hz) and around 80 Hz in the [(S),S(R)]-epimers (in 12 Δv = 79 Hz). (a) Colobert, F.; Des Mazery, R.; Solladié, G.; Carreno, M. C. Org. Lett. 2002, 4, 1723. (b) Solladié, G.; Gressot, L.; Colobert, F. Eur. J. Org. Chem. 2000, 357. (c) Solladié, G.; Adamy, M.; Colobert, F. J. Org. Chem. 1996, 61, 4369. (d) Solladié, G.; Colobert, F.; Denni, D. Tetrahedron: Asymmetry 1998, 9, 3081.
33. 11a-d we noticed that the nonequivalence of the methylene hydrogens α to the sulfoxide group is quite different in the two diastereomers: in the [(R),S(R)]-configuration the Δv value between these two hydrogens is around 40 Hz (in 13, Δv = 50 Hz) and around 80 Hz in the [(S),S(R)]-epimers (in 12 Δv = 79 Hz). (a) Colobert, F.; Des Mazery, R.; Solladié, G.; Carreno, M. C. Org. Lett. 2002, 4, 1723. (b) Solladié, G.; Gressot, L.; Colobert, F. Eur. J. Org. Chem. 2000, 357. (c) Solladié, G.; Adamy, M.; Colobert, F. J. Org. Chem. 1996, 61, 4369. (d) Solladié, G.; Colobert, F.; Denni, D. Tetrahedron: Asymmetry 1998, 9, 3081.
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