The stereoselective cyclopropanation of chiral allylic alcohols using a chiral dioxaborolane ligand: A new route to anti-cyclopropylmethanol derivatives

Tetrahedron

Volumn 55, Issue 29, 1999, Pages 8845-8856

  Charette, André B ^a   Lebel, Hélène ^a   Gagnon, Alexandre ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

Alcohols; Cyclopropanation; Cyclopropanes; Zinc and compounds

Indexed keywords

ALLYL ALCOHOL; BORANE DERIVATIVE; CYCLOPROPANE DERIVATIVE; METHANOL DERIVATIVE;

CHIRALITY; CONFERENCE PAPER; DERIVATIZATION; DRUG SYNTHESIS; GAS CHROMATOGRAPHY; LIGAND BINDING; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0033575496     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00448-2     Document Type: Conference Paper

References (23)

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15. Indirectly, anti-Z-cyclopropane are accessible by reduction of Z-cyclopropyl ketones: Lautens. M.; Delanghe, P. H. M. Tetrahedron Lett. 1994, 35, 9513-9516.
16. 2). In this case, it is not very probable that this reaction is directed by the silyl ether. The minimization of the A-1,3 strain and attack by the reagent anti to the TIPS ether explains the stereochemical outcome of this reaction.
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19. (c) Mareda, J.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1983, 105, 6997-6999.
20. Allylic alcohols used in entries 1-4, 7-10 were prepared by a Sharpless kinetic resolution: Gao, Y.; Hanson, R. M.; Kunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780.
21. The allylic alcohol used in entry 5 and 6 was prepared in 90% ee according to the following procedure and then further enriched by a Sharpless kinetic resolution (ref. 9): Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691-5700.
22. 2O (59%). McKew, J. C.; Kurth M. J. Org. Prep. P Roc. Int. 1993, 25, 125-130.
23. 2·DME complex must be used. See ref. 1c for the procedure.