The cyclopropanation of silyl enol ethers of cisoid or labile α-ethylenic ketones. A general and rapid route to cyclobutanones and cyclopentanones.

Girard, Christian; Amice, Philippe; Barnier, J. P.; Conia, J. M.

doi:10.1016/s0040-4039(01)91899-4

Cited by 48 publications

(10 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Compound 9c: mp 133-134 °C; IR (Kbr) 3460, 1725 (sh), 1715 cm"1; NMR (CDCL) 0.90 (s, 3 ), 1.12 (s, 3 ), 1.85 (s, 3 ), 1.85 (d, 1 H, J = 16 Hz), 2.44 (s, 2 ), 3.06 (d, 1 H, J = 16 Hz), 3.82 (d, 1 H, J = 7 Hz, -OH), 4.10 (d, 1 H, J = 7 Hz), 7.2-S.2 (m, 5 H); mass spectrum m/e (rel abundance) 276 (M+, 3), 155 (10), 154 (100), 139 (11).…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Reaction of trimethylsilyloxy-1,3-dienes with lead(IV) benzoate

Rubottom¹,

GRUBER²

1977

J. Org. Chem.

View full text Add to dashboard Cite

Section: Methodsmentioning

confidence: 99%

“…183 (16), 182 (M+, 100), 181 (12), 167 167 (30), 165 (8), 151 (7), 75 (7), 73 are, respectively, 930-68-7, 1193-18-6, 78-59-1, 31883-98-4, 5259-65-4, 932-66-1, 1896-62-4. S Registry no.…”

unclassified

Reaction of trimethylsilyloxy-1,3-dienes with lead(IV) benzoate

Rubottom¹,

GRUBER²

1977

J. Org. Chem.

View full text Add to dashboard Cite

“…In this chemistry, cyclopropane 4 8,9 was treated with an acetal in the presence of Lewis acid. Conversion of the acetal to a reactive oxonium ion and attachment of 4 yields a cyclopropyl cation that undergoes ring expansion to afford a mixture of three spirocyclobutanone diastereomers, of which 5a was predominant.…”

mentioning

confidence: 99%

A Tandem Prins/Schmidt Reaction Approach to Marine Alkaloids: Formal and Total Syntheses of Lepadiformines A and C

Meyer

Katz

et al. 2010

Org. Lett.

View full text Add to dashboard Cite

The tricyclic core of the cylindricine or lepadiformine families of alkaloid natural products was assembled via a Prins addition/intramolecular Schmidt rearrangement under Lewis acid conditions. Both single-pot and two-stage variations of this process were examined, with particular attention to the stereochemical outcome of the processes. This technology has been applied to a formal total synthesis of lepadiformine A and a total synthesis of lepadiformine C.

show abstract

“…[20][21][22] Fluorine substitution was reported to allow benign rearrangement conditions and render the C−C bond cleavage regioselective.…”

Section: Resultsmentioning

confidence: 99%

Metal-free synthesis of α,α-difluorocyclopentanone derivatives via regioselective difluorocyclopropanation/VCP rearrangement of silyl dienol ethers

Takayama¹,

Fuchibe²,

Ichikawa³

2017

Arkivoc

View full text Add to dashboard Cite

Silyl dienol ethers underwent chemoselective difluorocyclopropanation under mild conditions with difluorocarbene, which was generated from trimethylsilyl 2,2-difluoro-2-(fluorosulfonyl)acetate (TFDA) using 1,8-bis(dimethylamino)naphthalene (proton sponge) as a catalyst. Successive vinylcyclopropane/cyclopentene (VCP) rearrangements readily proceeded to provide biologically promising 5,5-difluorocyclopent-1-en-1-yl silyl ethers in a one-pot operation without the use of metal catalysts.

show abstract

The cyclopropanation of silyl enol ethers of cisoid or labile α-ethylenic ketones. A general and rapid route to cyclobutanones and cyclopentanones.

Cited by 48 publications

References 22 publications

Reaction of trimethylsilyloxy-1,3-dienes with lead(IV) benzoate

Reaction of trimethylsilyloxy-1,3-dienes with lead(IV) benzoate

A Tandem Prins/Schmidt Reaction Approach to Marine Alkaloids: Formal and Total Syntheses of Lepadiformines A and C

Metal-free synthesis of α,α-difluorocyclopentanone derivatives via regioselective difluorocyclopropanation/VCP rearrangement of silyl dienol ethers

Contact Info

Product

Resources

About