C2-symmetric bis-sulfoxide: A novel chiral auxiliary for asymmetric desymmetrization of cyclic meso-1,2-diols

Journal of Organic Chemistry

Volumn 65, Issue 11, 2000, Pages 3284-3291

  Maezaki, Naoyoshi ^a   Sakamoto, Atsunobu ^a   Nagahashi, Noboru ^a   Soejima, Motohiro ^a   Li, Ying Xia ^a   Imamura, Tsuneaki ^a   Kojima, Naoto ^a   Ohishi, Hirofumi ^b   Sakaguchi, Ken Ichi ^a   Iwata, Chuzo ^a   Tanaka, Tetsuaki ^a  

^a OSAKA UNIVERSITY   (Japan)

^b OSAKA MEDICAL COLLEGE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; SULFOXIDE;

ACETYLATION; ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATION; HYDROLYSIS; ORGANIC CHEMISTRY; OXIDATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034595952     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9919409     Document Type: Article

References (44)

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40. The reaction should be carried out below 5°C to avoid partial racemization of 1.
41. In the absence of crown ether, the acetate 8a-Ac was formed in a poor yield (56%) and a considerable amount of acetal 7a was recovered (28%).
42. 4Cl aqueous solution. This workup was essential to prevent undesirable recyclization of the product. The partially acetylated product was filtrated through a short pad of silica gel and then completely acetylated with acetic anhydride and DMAP.
43. The absolute configurations of the benzyl ethers 8a-Bn, 8c, and 8e-f were established by Mosher's method after removal of the chiral auxiliary with 10% HCl followed by conversion into the MTPA esters. Those of the acetates 8a-Ac and 8b were determined by Mosher's method after converting the alkoxides from 7a and 7b into the corresponding MTPA esters. The stereochemistry of 8d was assumed by analogy with others: Dale, J. A.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549; J. Am. Chem. Soc. 1973, 95, 512-519.
44. The absolute configurations of the benzyl ethers 8a-Bn, 8c, and 8e-f were established by Mosher's method after removal of the chiral auxiliary with 10% HCl followed by conversion into the MTPA esters. Those of the acetates 8a-Ac and 8b were determined by Mosher's method after converting the alkoxides from 7a and 7b into the corresponding MTPA esters. The stereochemistry of 8d was assumed by analogy with others: Dale, J. A.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549; J. Am. Chem. Soc. 1973, 95, 512-519.