STEREOSELECTIVE RADICAL ADDITIONS USING CHIRAL 1,3-DIOXOLANONES DERIVED FROM LACTIC AND MALIC-ACID

KNEER G, Mattay J, HEIDBREDER A, RAABE G, KREBS B, LAGE M (1995)
Journal für praktische Chemie 337(1): 113-124.

Journal Article | Published | English

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Abstract
The hydrogen abstraction of radical intermediates yielded by radical addition to the methylene compound 6, shows excellent facial selectivity. Conformational analyses of the radical intermediates were carried out by quantum chemical calculations and explain these results. The chiral radicals 7 and 8, yielded from the chiral bromides 3 and 4, lead with ethyl acrylate to the adducts 28 and 29 with more 96 % de. The adduct 28 was converted to the optically active gamma-valerolactone 30. The structures of the bromides 3, 4 and 31 as well as the radical adducts 19a, 24 and 25 have been verified by X-ray diffraction analysis.
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KNEER G, Mattay J, HEIDBREDER A, RAABE G, KREBS B, LAGE M. STEREOSELECTIVE RADICAL ADDITIONS USING CHIRAL 1,3-DIOXOLANONES DERIVED FROM LACTIC AND MALIC-ACID. Journal für praktische Chemie. 1995;337(1):113-124.
KNEER, G., Mattay, J., HEIDBREDER, A., RAABE, G., KREBS, B., & LAGE, M. (1995). STEREOSELECTIVE RADICAL ADDITIONS USING CHIRAL 1,3-DIOXOLANONES DERIVED FROM LACTIC AND MALIC-ACID. Journal für praktische Chemie, 337(1), 113-124.
KNEER, G., Mattay, J., HEIDBREDER, A., RAABE, G., KREBS, B., and LAGE, M. (1995). STEREOSELECTIVE RADICAL ADDITIONS USING CHIRAL 1,3-DIOXOLANONES DERIVED FROM LACTIC AND MALIC-ACID. Journal für praktische Chemie 337, 113-124.
KNEER, G., et al., 1995. STEREOSELECTIVE RADICAL ADDITIONS USING CHIRAL 1,3-DIOXOLANONES DERIVED FROM LACTIC AND MALIC-ACID. Journal für praktische Chemie, 337(1), p 113-124.
G. KNEER, et al., “STEREOSELECTIVE RADICAL ADDITIONS USING CHIRAL 1,3-DIOXOLANONES DERIVED FROM LACTIC AND MALIC-ACID”, Journal für praktische Chemie, vol. 337, 1995, pp. 113-124.
KNEER, G., Mattay, J., HEIDBREDER, A., RAABE, G., KREBS, B., LAGE, M.: STEREOSELECTIVE RADICAL ADDITIONS USING CHIRAL 1,3-DIOXOLANONES DERIVED FROM LACTIC AND MALIC-ACID. Journal für praktische Chemie. 337, 113-124 (1995).
KNEER, G, Mattay, Jochen, HEIDBREDER, A, RAABE, G, KREBS, B, and LAGE, M. “STEREOSELECTIVE RADICAL ADDITIONS USING CHIRAL 1,3-DIOXOLANONES DERIVED FROM LACTIC AND MALIC-ACID”. Journal für praktische Chemie 337.1 (1995): 113-124.
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