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Enantioselective deprotonation of the monoacetals of bicyclo[3.3.0]octan-3,7-dione. An approach to the asymmetric synthesis of chiral synthons for carbacyclins
- Issue Date
- Sep-1989
- Publisher
- Elsevier BV
- Citation
- Tetrahedron Letters, v.30, no.51, pp 7221 - 7224
- Pages
- 4
- Journal Title
- Tetrahedron Letters
- Volume
- 30
- Number
- 51
- Start Page
- 7221
- End Page
- 7224
- ISSN
- 0040-4039
- Abstract
- Kinetic deprotonation of the monoacetals (4) of bicyclo[3.3.0]octan-3,7-dione by chiral lithium amides (5) in the presence of excess trimethylsilyl chloride afforded the corresponding silyl enol ethers (6), useful synthons for the synthesis of optically active carbacyclins, in up to 94% ee.
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