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Tetrahedron Letters

Volumn 18, Issue 40, 1977, Pages 3549-3552

Highly regioselective additions of certain 2-lithio-1,3-dithianes to conjugated ketones

(2) Ostrowski, Paul C a Kane, Vinayak V a

a Ortho McNeil Pharmaceutical Incorporated (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002227620 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(01)83289-5 Document Type: Article

Times cited : (58)

References (28)

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2
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- and references cited in
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10
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- Ketene Thioacetals by ?Peterson Carbonyl Olefination? with Metalated Formyl Trimethylsilyl Thioacetals
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11
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12
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13
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- Synthese der 2-Methyl-lysergs�ure Eine neueFriedel-Crafts-Methode. 74. Mitteilung �ber Mutterkornalkaloide
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14
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- A GENERAL ESTER SYNTHESIS VIA 2-LITHIO-2-METHYLTHIO-1,3-DITHIANE
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15
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- Conjugate addition of tris(phenylthio)methyl-lithium to ??-unsaturated ketones. Synthesis of ?-keto-esters
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- Manas¹ Smith²

16
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- Michael Additions of Metalated Thioacetals to Cyclic Enones
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- Seebach¹ Burtinghaus²

17
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- For other reports of the 1,4-addition of sulfur-stabilized carbanions to α,β-unsaturated ketones see:
- (1972) J. Amer. Chem. Soc. , vol.94 , pp. 8461
- Mukaiyama¹ Narasaku² Furusato³

18
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19
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20
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- We thank Professor E.L. Eliel for informing us of his results prior to publication
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- Sauvetre¹ SeydenPenne²

21
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- After the completion of this work, a paper describing the conjugate and direct addition of ester enolates to cyclohexenone was reported; see
- (1976) J. Org. Chem. , vol.41 , pp. 4044
- Schultz¹ Yee²

22
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- (1966) J. Org. Chem. , vol.31 , pp. 4303
- Seebach¹ Erickson² Singh³

23
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- Normal workup involves extraction of the reaction mixture with ether, evaporation of the organic layer and chromatography of the crude product on SilicAR CC-7 (Mallinckrodt). A small amount of the starting dithiane is eluted first followed by the desired product.

24
- 84918284948
- 2-Lithio-2-thienyl-1,3-dithiane (5) and 2-lithio-2-α-naphthyl-1,3-dithiane (6) were prepared by the addition of n-butyllithium to 2-thienyl-1,3-dithiane and 2-α-naphthyl-1,3-dithiane in THF. These aromatic dithianes are readily prepared from the corresponding aromatic aldehyde and propane-1,3-dithiol following the procedure in reference 6.

25
- 84918284947
- Satisfactory elemental analyses were obtained for allnew compounds and spectral data were consistent with the assigned structures.

26
- 84918284946
- A yield of less than 5% of 1,4-addition product was obtained when lithiated-tris-(phenylthio)- methane was reacted with 3-methyl-2-cyclohexenone, see reference 3.

27
- 84918284945
- Pathway A cannot be completely ruled out at present until further experiments such as chemically induced dynamic nuclear polarization (CIDNP) are carried out. We thank Professor J.E. Baldwin (MIT) for making us aware of this pathway.

28
- 84918284944
- We thank Mr. D.L. Doyle for repeating and confirming this result.

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