A Samarium-Mediated, Highly Stereoselective Reaction of 1,1-Dihaloalkanes with Aldehydes: Generation of a Chiral α-Iodoethyl Building Block from Achiral 1,1-Diiodoethane

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 6, 1997, Pages 617-618

  Matsubara, Seijiro ^a   Yoshioka, Masahito ^a   Utimoto, Kiitiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Asymmetric synthesis; Iodine; Lanthanides; Samarium

Indexed keywords

EID: 0030933939     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199706171     Document Type: Article

References (38)

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33. 2 and geminal dihaloalkanes has not been reported [5]. The structure of the intermediate is not clear but assumed to be α-iodoethylsamarium diiodide.
34. 1H NMR analysis of the crude product and stereospecific conversion of iodohydrin into the corresponding epoxide by a treatment with NaH in THF/hexamethyl phosphoric triamide.
35. 3SnH.
36. 2 ratios were as follows: 1.0/1.0/2.0 mmol: 31% (99:1); 1.0/2.0/4.0 mmol: 47% (99:1); 1.0/3.0/ 6.0 mmol: 62% (99:1). If excess reagent was used, 1-iodo-2-phenylpropane and 2,5-diphenyl-3-hexene were observed as by-products. The reduction of diastereotopic iodide may not proceed selectively, and the unfavored intermediate might decompose into these by-products.
37. 2 did not afford halohydrin. Instead, a reduction of aldehyde to form alcohol was detected. Addition of a catalytic amount of a Co(II) compound allowed the addition to proceed. The catalyzed reaction gave syn-iodohydrin selectively: M. Yoshioka, M. Horiuchi, S. Matsubara, K. Utimoto, unpublished results.
38. 2-aldehyde complex or by the preferred reaction of one enantiomer of the α-iodoalkylsamarium species and facile racemization of the other. Mechanistic studies are underway.