✦ LIBER ✦

Syntheses of Cyclopropyl Silyl Ketones

✍ Scribed by Markus E. Scheller; Bruno Frei

Publisher: John Wiley and Sons
Year: 1986
Tongue: German
Weight: 651 KB
Volume: 69
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19860690107

No coin nor oath required. For personal study only.

✦ Synopsis

The synthesis of the cyclopropyl silyl ketones 1 4 is described. The trimethylsilyl ketone 1 was prepared from geraniol ((E)-5) in ca. 10% overall yield by cyclopropanation leading to 6 , Cr03 oxidation to the aldehyde 8, reaction of the latter with trimethylsilyl anion to 14A + B, and CrO? oxidation to 1. Also for the (t-bu-ty1)dimethylsilyl ketones 2 4, an efficient four-step synthesis with overall yields of 48%, 85%, and 13%, respectively, was elaborated, starting from the allylic alcohols (E)-5, (Z)-5, and 23. The method of preparation involves as the key step a Wittig rearrangement of the silylallyl ethers ( ( E / Z ) -2 0 , 24) to the silyl alcohols ((E/Z)-21, 25), subsequent cyclopropanation (19A + B, 22A + B, 26), and oxidation to the cyclopropyl silyl ketones 2 4 .

📜 SIMILAR VOLUMES

Syntheses of α, β-Epoxy Silyl Ketones

✍ Markus E. Scheller; W. Bernd Schweizer; Bruno Frei 📂 Article 📅 1989 🏛 John Wiley and Sons 🌐 German ⚖ 462 KB

The terms A, B, and C are used for the description of diastereoisomers, whose configurations were not assigned conclusively. ## ' ) Due to the low amounts of pure 5A + Bin our hands, the oxidation was not repeated with CrO,/pyridine, the reagent which would have led to a higher yield of 2. MHz):

Photochemical reactions. 152nd Communica

Photochemical reactions. 152nd Communication. Photochemistry of acylsilanes; photolysis and thermolysis of cyclopropyl silyl ketones

✍ Markus E. Scheller; Bruno Frei 📂 Article 📅 1990 🏛 John Wiley and Sons 🌐 German ⚖ 587 KB

## Abstract The photolysis and thermolysis of the Cyclopropyl silyl ketones 3, 4, and 5 are described. On __n__,π\* excitation, the silyl ketones 3 and 4 undergo a __Norrish__‐type‐II reaction involving γ‐H abstraction, cyclopropyl ring cleavage followed by retro‐enolization to the acylsilanes 6 an

ChemInform Abstract: α-Silyl Ketone Cont

ChemInform Abstract: α-Silyl Ketone Controlled Asymmetric Syntheses

✍ Dieter Enders; Johannes Adam; Daniela Klein; Thomas Otten 📂 Article 📅 2000 🏛 John Wiley and Sons ⚖ 25 KB

ChemInform Abstract: Palladium-Catalyzed

ChemInform Abstract: Palladium-Catalyzed Preparation of Silyl Enolates from α,β-Unsaturated Ketones or Cyclopropyl Ketones with Hydrosilanes.

✍ Yuto Sumida; Hideki Yorimitsu; Koichiro Oshima 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 57 KB 👁 1 views

An Efficient Synthesis of 5-Silyl-2,3-di

An Efficient Synthesis of 5-Silyl-2,3-dihydrofurans via Acid-Catalyzed Ring-Enlargement of Cyclopropyl Silyl Ketones and Their Functionalization.

✍ Mitsunori Honda; Tomoyuki Naitou; Hiromitsu Hoshino; Seiji Takagi; Masahito Segi 📂 Article 📅 2006 🏛 John Wiley and Sons ⚖ 32 KB

Photochemical Synthesis of Highly Functi

Photochemical Synthesis of Highly Functionalized Cyclopropyl Ketones.

✍ Pablo Wessig; Olaf Muehling 📂 Article 📅 2003 🏛 John Wiley and Sons ⚖ 270 KB