Syn-Effect” in the Conversion of (E)-α,β-Unsaturated Esters into the Corresponding β,γ-Unsaturated Esters and Aldehydes into Silyl Enol Ethers

SK Guha, A Shibayama, D Abe… - Bulletin of the …, 2004 - academic.oup.com
The stereochemistry in the conversion of (E)-α, β-unsaturated esters into the corresponding
β, γ-unsaturated esters, and that in the conversion of aldehydes into the silyl enol ethers …

Stereoselective Synthesis of (2Z,4E)-2,4-Pentadien-1-ols via Sequential 1,4-Elimination Reaction and [1,2]-Wittig Rearrangement Starting from (E)-4-Alkoxy-2 …

T Nakano, T Soeta, K Endo, K Inomata… - The Journal of Organic …, 2013 - ACS Publications
The sequential 1, 4-elimination reaction of (E)-4-alkoxy-2-butenyl benzoates and [1, 2]-Wittig
rearrangement gave (2 Z, 4 E)-2, 4-pentadien-1-ols stereoselectively. Z-Selective formation …

Synthesis of Benzo[a]carbazoles from 2‐Arylindoles via a Sequential Propargylation, Propargyl‐Allenyl Isomerization, and 6π‐Electrocyclization

JW Lim, SH Kim, J Kim, JN Kim - Bulletin of the Korean …, 2015 - Wiley Online Library
An efficient two‐step synthetic approach of benzo [a] carbazoles from 2‐arylindoles has
been developed. The first step is a propargylation of 2‐arylindoles at the 3‐position …

“Syn–Effect” in the Base–Induced Isomerization of Vinylic Sulfones to Allylic Sulfones and the Related Various Reactions

K Inomata - Journal of Synthetic Organic Chemistry, Japan, 2009 - jstage.jst.go.jp
“Syn–effect” has been recognized as a major cause of stabilizing the syn–conformation at
the transition state of a number of reactions against the steric hindrance. This account deals …

Stereoselective One-pot 1,4-Elimination and the [1,2]-Wittig Rearrangement of (E)-δ-(Arylmethoxy or 3-Silyl-2-propynyloxy)-substituted Allylic Sulfones

S Horii, I Ishimaru, Y Ukaji, K Inomata - Chemistry Letters, 2011 - academic.oup.com
The successive treatment of (E)-δ-(arylmethoxy)-substituted allylic sulfones with t-BuOK and
LDA afforded the corresponding (Z)-2, 4-dienyl alcohols with high stereoselectivities via 1, 4 …

Diastereoselective β-hydroxy vinylsulfone isomerizations

GW O'Neil, TD Clark, AP Jones, C Wallace… - Organic & …, 2025 - pubs.rsc.org
Vinylic phenylsulfones containing a β-hydroxyl stereocenter undergo a diastereoselective
isomerization to the corresponding allylic isomer upon treatment with 1, 8-diazabicyclo (5.4 …

“Syn Effect” in Nucleophilic Addition of Amines to 1,3-Dienyl Sulfone and Ethyl (E)-2,4-Pentadienoate

M Yamazaki, SK Guha, Y Ukaji… - Bulletin of the Chemical …, 2008 - academic.oup.com
The stereochemistry of nucleophilic addition of amines to (E)-1-tosyl-1, 3-butadiene was
investigated. The Z/E ratios of the resulting allylic sulfones varied with amines, solvents …

Palladium-Catalyzed Elimination Reaction of Acyclic (E)-Allylic Acetates: The Stereochemistry Elucidated by “Syn-Effect”

H Takenaka, Y Ukaji, K Inomata - Chemistry letters, 2005 - academic.oup.com
The stereochemistry of the elimination reaction of acyclic (E)-allylic acetates into the
corresponding 1, 3-dienes catalyzed by palladium in the presence of a base was …

“Syn Effect” in the 1,4-Eliminative Ring Opening of [3-Substituted (E)-1-Propenyl]oxiranes to the Corresponding 2,4-Dienyl Alcohols

N Takeda, T Chayama, H Takenaka, Y Ukaji… - Chemistry …, 2005 - academic.oup.com
Abstract Stereochemistry of the 1, 4-eliminative ring opening of [3-substituted (E)-1-propenyl]
oxiranes to the corresponding 2, 4-dienyl alcohols by LDA was investigated. The Z/E ratios …

A Unified Strategy Toward 5‐, 6‐, and 7‐Membered Nitrogen Heterocycles Through Free Radical then Metal‐Mediated Functionalization of Ene‐carbamates

R Beniazza, C Poittevin, J Lusseau… - Advanced Synthesis …, 2017 - Wiley Online Library
Free‐radical carbo‐alkenylation of N‐aryl‐, N‐benzyl‐, and N‐phenethyl‐ene‐carbamates
with a disulfone provides vinyl sulfones which may then be functionalized and engaged in …