131674-12-9

Upstream product

• 131692-90-5 (Z)-3-iodo-3-phenylprop-2-en-1-ol 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 5908-41-8 benzoyltrimethylsilane 
• 62713-14-8 ethyl (Z)-3-phenyl-3-(trimethylsilyl)prop-2-enoate 
• 4071-88-9 trimethylsilanyl-acetic acid ethyl ester 
• 131674-26-5 ((Z)-3-Iodo-3-phenyl-allyloxy)-trimethyl-silane 
• 75-77-4 chloro-trimethyl-silane 

Downstream Products

• 1028254-99-0 Trimethyl-((E)-5-methyl-3-phenyl-hexa-2,5-dienyloxy)-silane 

Relevant academic research and scientific papers

Improved catalysts for the iridium-catalyzed asymmetric isomerization of primary allylic alcohols based on charton analysis

An improved generation of chiral cationic iridium catalysts for the asymmetric isomerization of primary allylic alcohols is disclosed. The design of these air-stable complexes relied on the preliminary mechanistic information available, and on Charton analyses using two preceding generations of iridium catalysts developed for this highly challenging transformation. Sterically unbiased chiral aldehydes that were not accessible previously have been obtained with high levels of enantioselectivity, thus validating the initial hypothesis regarding the selected ligand-design elements. A rationale for the high enantioselectivities achieved in most cases is also presented. Achieving enantioselectivity: An improved generation of chiral cationic iridium catalysts for the asymmetric isomerization of primary allylic alcohols is disclosed. The design of these air-stable complexes relies on preliminary mechanistic information and on Charton analyses using two preceding generations of iridium catalysts developed for this highly challenging transformation (see figure).

Copper(I) tert-butoxide-promoted 1,4 Csp-to-O silyl migration: Generation of vinyl copper equivalents and their stereospecific cross-coupling with allylic, aryl, and vinylic halides

Successive treatment of the (Z)-γ-trimethylsilyl allylic alcohols with copper(I) tert-butoxide and allylic halides followed by the tetrabutylammonium fluoride-assisted hydrolysis produced the allylation products, 2,5-alkadien-1-ols, with complete retention of configuration. Similar treatment of the organometallic intermediates with aryl and vinylic halides in the presence of palladium(O) catalyst gave the corresponding cross-coupling products in good yields. The stereoselective preparation of the starting materials is also described.

Copper(I) tert-butoxide-promoted 1,4 Csp2-to-O silyl migration: Stereospecific allylation of (Z)-γ-trimethylsilyl allylic alcohols

Formula presented The cyclic silyl ethers, 2,2-dimethyl-1-oxa-2-sila-3-cyclopentenes, were produced by the treatment of (Z)-γ-trimethylsilyl allylic alcohols with a catalytic or stoichiometric amount of lithium tert-butoxide. On the other hand, successive

Synthesis of Silicon Substituted Cyclopropylmethyl Alcohols in Optically Active Form via Asymmetric Simmons-Smith Reaction of γ-Silicon Substituted Allylic Alcohols

Optically active silicon substituted cyclopropyl methyl alcohols were synthesized through asymmetric Simmons-Smith reaction; that is, the reaction of γ-silicon substituted allylic alcohols with diethylzinc and diiodomethane utilizing (+)-diethyl tartrate

Stereoselective Synthesis of Terminal 1,3-Butadienes by the Condensation Reaction of Aldehydes and Ketones with the γ-Trimethylsilyl-Substituted Allylboranes

Allylboranes 7-12, readily prepared from allenylsilanes 1-6 by hydroboration with 9-borabicyclononane, smoothly condense with aldehydes and ketones to afford, after basic or acidic workup to promote the Peterson olefination reaction, a variety of t

A NEW STEREOSELECTIVE SYNTHESIS OF (Z)-VINYLSILANE ALLYLIC ALCOHOLS

A new, highly stereoselective method for the synthesis of (Z)-vinylsilane allylic alcohols 3 is described.This approach to such γ-silylated allylic alcohols employs a novel 1,4-O -> sp2C silyl rearrangement of appropriate silyl ether precursors