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Tetrahedron Letters

Volumn 29, Issue 49, 1988, Pages 6467-6470

A facile entry to β,δ-diketo and syn-β,δ-dihydroxy esters

(2) Hanamoto, Takeshi a Hiyama, Tamejiro a

a SAGAMI CHEMICAL RESEARCH CENTER (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000137149 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)82375-8 Document Type: Article

Times cited : (54)

References (17)

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- Willard, A.K.; Novello, F.C.; Hoffman, W.F.;Cragoe, E.J. US Patent 4,375,475 (1983)

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- Chen¹ Hardtmann² Prasad³ Repic⁴ Shapiro⁵

4
- 0001633976
- A novel method for the in situ generation of alkoxydialkylboranes and their use in the selective preparation of 1,3-syn diols.
- (1987) Chemistry Letters , pp. 1923
- Chen¹ Gunderson² Hardtmann³ Prasad⁴ Repic⁵ Shapiro⁶

5
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- Günther, W.; Ernold, G.; Gerhard, B.; Hans-Hermann, L., Deutschesatent DE 3530798 A1.

6
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- Baader¹ Bartmann² Beck³ Bergmann⁴ Jendralla⁵ Kesseler⁶ Wess⁷ Schubert⁸ Granzer⁹ Kerekjarto¹⁰ Krause¹¹

7
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- and references cited therein
- (1987) Tetrahedron Lett. , vol.28 , pp. 1385
- Lynch¹ Volante² Wattley³ Shinkai⁴

8
- 0000691988
- (1987) J. Med. Chem. , vol.30 , pp. 1858
- Heathcock¹ Hadley² Rosen³ Theisen⁴ Hecker⁵

9
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- (1988) Tetrahedron Lett. , vol.29 , pp. 3757
- Johnson¹ Kelson² Elliott³

10
- 0000425224
- (1984) Tetrahedron , vol.40 , pp. 2233
- Narasaka¹ Pai²

11
- 84987466985
- Stereoselective Reduction of ?-Hydroxy-?-ketoesters
- (1986) Helvetica Chimica Acta , vol.69 , pp. 803
- Kathawala¹ Prager² Prasad³ Repic⁴ Shapiro⁵ Stabler⁶ Widler⁷

12
- 0000906961
- (1986) Tetrahedron Lett. , vol.27 , pp. 3009
- Kiyooka¹ Kuroda² Shimasaki³

13
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- Condensation of nitriles with the dianions 2-2″ in the presence of zinc ion is claimed in a patent. Verhoeven, T.R.; McNamara, J.M. Eur. Pat. Appl. EP 204,287. However, we found it hard to reproduce the results.

14
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- Synthesis of phenols by polyketide condensation and an efficient synthesis of 3,5-dioxoalkanoates from amides.
- (1985) Chemistry Letters , pp. 1145
- Yamaguchi¹ Shibato² Hirao³

15
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- Nahm¹ Weinreb²

16
- 84918159528
- 1H NMR disclosed that the δ-carbonyl groups of 3a-f are enolized. Our design of the reaction is following. An exchange reaction between the enol moiety and diethylmethoxyborane should afford a vinyloxyborane intermediate, the β-carbonyl group of which would be reduced first to give, after protonation, a β-hydroxy ketone intermediate requisit to the syn-reduction.

17
- 84918159527
- By using chiral dialkyl(methoxy)borane, the asymmetric reduction is feasible. We have observed that a methoxyborane derived from (S)-(-)-limonene certainly gives syn-diols (selectivity 〉95%) albeit of only 8% ee.

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