Novel asymmetric desymmetrization of meso-1,2-diols via diastereoselective β-elimination of chiral α-arylsulfinyl acetals

Tetrahedron

Volumn 52, Issue 19, 1996, Pages 6527-6546

  Maezaki, Naoyoshi ^a   Soejima, Motohiro ^a   Takeda, Miwako ^a   Sakamoto, Atsunobu ^a   Matsumori, Yûki ^a   Tanaka, Tetsuaki ^a   Iwata, Chuzo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029919217     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00294-3     Document Type: Article

References (51)

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37. β-Ketosulfoxides 1 and 2 were prepared as previously described by the reaction of the corresponding esters with enantiomerically pure (R)-methyl p-tolyl sulfoxide (Solladié, G. Synthesis 1981, 185-196.) in the presence of LDA. The optical purity was determined by comparison with the reported specific rotation (Banfi, L.; Colombo, L.; Gennari, C.; Annunziata, R.; Cozzi, F. Synthesis 1982, 829-831. Kunieda, N.; Nokami, J.; Kinoshita, M Chem. Lett. 1974, 369-372.).
38. β-Ketosulfoxides 1 and 2 were prepared as previously described by the reaction of the corresponding esters with enantiomerically pure (R)-methyl p-tolyl sulfoxide (Solladié, G. Synthesis 1981, 185-196.) in the presence of LDA. The optical purity was determined by comparison with the reported specific rotation (Banfi, L.; Colombo, L.; Gennari, C.; Annunziata, R.; Cozzi, F. Synthesis 1982, 829-831. Kunieda, N.; Nokami, J.; Kinoshita, M Chem. Lett. 1974, 369-372.).
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40. The stereochemistry of the acetals in 4-7a and 4-7b was determined based on nuclear Overhauser effect (NOE) experiments, in which marked NOE enhancements were observed between the angular methine protons on the bicyclic ring and the substituent R or the sulfinylmethyl group (Fig. 1). (matrix presented) Fig. 1. NOE Observaon of α-Sulfinyl Actals.
41. *) to minimize the steric interaction, therby affording mainly the acetals with the endo-larger group (RL). The higher selectivity for the acetal 5b is due to the great difference in size between the phenyl group (RL) and the sulfinylmethyl group (Rs) (Fig.2). (matrix presented) Fig. 2. Plausible Reaction Mechanism for Acetalization.
42. The stereochemistry of the olefin in 8b, 10a-b, and 11a-c was determined by NOE experiment (Fig. 3). (matrix presented) Fig. 3. Geometry of the Olefin Moieties.
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46. 2S; c) Raney Ni (W2), EtOH, room temp. Scheme 9
47. 2S. Scheme 10
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