ChemInform Abstract: Synthetic Studies Toward Pectenotoxin 2. Part 1. Stereocontrolled Access to the C<sub>10</sub>—C<sub>22</sub> Fragment.

Aho, Jatta E.; Salomaeki, Elina; Rissanen, Kari; Pihko, Petri M.

doi:10.1002/chin.200906213

Search citation statements

Order By: Relevance

Paper Sections

Select...

■ Experimental Section1

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2019

Publication Types

Select...

Article1

Relationship

Self Cite0

Independent1

Authors

Journals

Cited by 1 publication

(1 citation statement)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The physical and spectral data were consistent with those previously reported. 21 Benzyl(2-(chloromethyl)allyl)sulfane (S7). To a suspension of Cs 2 CO 3 (1.295 g, 5.8 mmol) in DMF (15 mL) were added 3-chloro-2-chloromethyl-1-propene (0.50 mL, 4.3 mmol) and benzyl mercaptan (0.55 mL 4.73 mmol).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

One-Pot Twofold Unsymmetrical C–Si Bond 2,6-Bifunctionalization of Arenes via Sequential [1,4]-Csp² to O-Silyl Migration

Wang

et al. 2019

J. Org. Chem.

View full text Add to dashboard Cite

Twofold unsymmetrical C−Si bond bifunctionalization of 2,6-di(trimethylsilyl) benzyl alcohols has been achieved in one pot via sequential [1,4]-Csp 2 to O-silyl migration. The hydroxyl group functions as an "on−off−on" switch to control two successive silyl migrations, and 4,7dimethyl-o-phenanthroline ligand favors cleavage of the endocyclic C−Si bond. Diverse Csp 3 /Csp 3 or Csp 2 /Csp 3 electrophiles can be installed at the 2-and 6-positions. This approach was used to chemoselectively functionalize the three C−Si bonds of 2,4,6-tri(trimethylsilyl) benzyl alcohol, transforming it into isochroman derivatives. The approach even works as a five-component reaction to construct complex symmetric structures.

show abstract

Section: ■ Experimental Sectionmentioning

confidence: 99%

One-Pot Twofold Unsymmetrical C–Si Bond 2,6-Bifunctionalization of Arenes via Sequential [1,4]-Csp² to O-Silyl Migration

Wang

et al. 2019

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: Synthetic Studies Toward Pectenotoxin 2. Part 1. Stereocontrolled Access to the C₁₀—C₂₂ Fragment.

Cited by 1 publication

References 1 publication

One-Pot Twofold Unsymmetrical C–Si Bond 2,6-Bifunctionalization of Arenes via Sequential [1,4]-Csp² to O-Silyl Migration

One-Pot Twofold Unsymmetrical C–Si Bond 2,6-Bifunctionalization of Arenes via Sequential [1,4]-Csp² to O-Silyl Migration

Contact Info

Product

Resources

About

ChemInform Abstract: Synthetic Studies Toward Pectenotoxin 2. Part 1. Stereocontrolled Access to the C10—C22 Fragment.

Cited by 1 publication

References 1 publication

One-Pot Twofold Unsymmetrical C–Si Bond 2,6-Bifunctionalization of Arenes via Sequential [1,4]-Csp2 to O-Silyl Migration

One-Pot Twofold Unsymmetrical C–Si Bond 2,6-Bifunctionalization of Arenes via Sequential [1,4]-Csp2 to O-Silyl Migration

Contact Info

Product

Resources

About

ChemInform Abstract: Synthetic Studies Toward Pectenotoxin 2. Part 1. Stereocontrolled Access to the C₁₀—C₂₂ Fragment.

One-Pot Twofold Unsymmetrical C–Si Bond 2,6-Bifunctionalization of Arenes via Sequential [1,4]-Csp² to O-Silyl Migration

One-Pot Twofold Unsymmetrical C–Si Bond 2,6-Bifunctionalization of Arenes via Sequential [1,4]-Csp² to O-Silyl Migration