Synthesis of new mixed (-)-menthylalkyltin dihydrides. stereoselective reduction of chiral and prochiral ketones

•Stereoselective reduction of chiral (-)-menthone.•Stereoselective reductions of prochiral acetophenone and 2-acetylnaphthalene. This paper reports de synthesis of a series of (-)-menthylalkyltin dihydrides, (-)-MenRSnH2 (R = Me, n-Bu, i-Pr, t-Bu, Neophyl), starting from (-)-menthyltrimethyltin. The...

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Bibliographic Details
Published in:Journal of organometallic chemistry 2021-03, Vol.935, p.121680, Article 121680
Main Authors: Terraza, V. Fabricio, Gerbino, Darío C., Podestá, Julio C.
Format: Article
Language:English
Subjects:
(-)-menthylalkyltin dihydrides
Reduction of (-)-menthone
Reduction of acetophenone, Reduction of 2-acetylnaphthalene
Use in stereoselective reductions
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Summary:•Stereoselective reduction of chiral (-)-menthone.•Stereoselective reductions of prochiral acetophenone and 2-acetylnaphthalene. This paper reports de synthesis of a series of (-)-menthylalkyltin dihydrides, (-)-MenRSnH2 (R = Me, n-Bu, i-Pr, t-Bu, Neophyl), starting from (-)-menthyltrimethyltin. The new (-)-menthylalkyltin dihydrides 12–16 were used in a study on the stereoselective reduction of chiral (-)-menthone under different reaction conditions. Also the results obtained in the reductions of prochiral acetophenone (27) and 2-acetylnaphthalene (28), with (-)-menthylmethyl- (12) and (-)-menthyli-propyltin (14) dihydrides are informed. Some physical properties as well as full 1H-, 13C-, and 119Sn NMR data of the new organotin compounds are informed. [Display omitted]
ISSN:0022-328X
1872-8561
DOI:10.1016/j.jorganchem.2021.121680