Cis and trans selective 1,4-addition of a lithium dithioester enolate to 4-O-TBS-2-cyclohexenone

Organic Letters

Volumn 8, Issue 18, 2006, Pages 3891-3894

  Spivey, Alan C ^a   Martin, Laetitia J ^a   Grainger, Damian M ^a   Ortner, Jörg ^b   White, Andrew J P ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748950998     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0611090     Document Type: Article

References (39)

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33. Interestingly, trans TBS ether 6t is very prone to desilylation on silica to give the corresponding alcohol whereas cis TBS ether 6c is not. The trans alcohol can, however, also be readily cyclized to trans lactone 7t (68%); see Supporting Information.
34. TBS ether deprotection/lactonization was performed essentially as in ref 8c but using HCl in place of HF.
35. 2C(OEt)OTBS and, therefore, obtained the Me ester (cf. Et ester in ref 8c).
36. Compound 5 crystallized with two independent molecules (I and II) in the asymmetric unit; molecule I is shown in Figure 2, and molecule II is shown in Figure S2 in the Supporting Information. The two molecules have essentially identical geometries (excluding the disorder in molecule II-see the Supporting Information) as can be seen by comparing the two images.
37. -1; see Stereochemistry of Organic Compounds; Eliel, E. L., Wilen, S. H., Eds.; Wiley: New York, 1994; p 696.
38. Cyclization to the 1-methylsulfanyl-2-thiabicyclo[3.3.1]nonan-3-one ring system (cf. 5) on warming does not require the presence of a 4-substituent; using 2-cyclohexenone itself cyclization also ensues (Spivey, A. C.; Martin, L. J. Unpublished).
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