Synthesis of optically active δ-dodecalactone via chiral resolution using CPF

Synlett

Volumn , Issue 15, 2007, Pages 2343-2346

  Nemoto, Hisao ^a   Zhong, Weihui ^a   Kawamura, Tomoyuki ^a   Kamiya, Masaki ^a   Nakano, Yasushi ^b   Sakamoto, Kei ^b  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

^b ZEON CORPORATION   (Japan)

Author keywords

Acetals; Alkenyl ethers; Chiral resolution; Flavor

Indexed keywords

ACETAL; ALKENYL GROUP; CYCLOPENTANE; DELTA DODECALACTONE; FURAN DERIVATIVE; LACTONE DERIVATIVE; PYRAN DERIVATIVE; SILICA GEL; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; COLUMN CHROMATOGRAPHY; OPTICAL RESOLUTION; OZONOLYSIS; SYNTHESIS;

EID: 34948827965     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-985604     Document Type: Article

References (24)

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13. The synthetic route shown in Scheme 1 was also applicable to all the lactones 1 (n = 3-6).
14. f value between the isopropyl esters 5a and 5b was as large as those between the corresponding methyl or ethyl esters. Thus, the high efficiency of chiral resolution of 3 is not due to the isopropyl ester moiety. Incidentally, the chemical yield of 3 from lactone 2 (85%) was much higher than the chemical yields of the corresponding methyl or ethyl esters (<8%), probably because reversible reaction from 3 to 2 is much slower than those from the corresponding methyl or ethyl esters to 2. This is the reason for the choice of the isopropyl ester.
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20. 2: 320.2715; found: 320.2691.
21. 36OSi: 284.2535; found: 284.2529.
22. 2Si: 286.2328; found: 286.2325.
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24. It is well known that compounds bearing a hydroxyl group at an asymmetric allylic or benzylic position can be separated more efficiently than saturated aliphatic alcohols when using most of the other chiral resolving agents. CPF has a similar tendency as described above. However, our investigations have shown that the separation efficiency of CPF is much greater than that of other agents. Chiral resolution of both 3 and 7 was successful and efficient, and we know no other reason for this high efficiency.