Construction of vicinal 4°/3°-carbons: Via reductive Cope rearrangement

Kristin M. Sobie; Matthew Albritton; Yinuo Yang; Mariana M. Alves; Adrian Roitberg; Alexander J. Grenning

doi:10.1039/d1sc06307c

Construction of vicinal 4°/3°-carbons: Via reductive Cope rearrangement

Kristin M. Sobie
, Matthew Albritton
, Yinuo Yang
, Mariana M. Alves
, Adrian Roitberg
, Alexander J. Grenning

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

Herein reported is a strategy for constructing vicinal 4°/3° carbons via reductive Cope rearrangement. Substrates have been designed which exhibit Cope rearrangement kinetic barriers of ∼23 kcal mol-1 with isoenergetic favorability (ΔG ∼ 0). These fluxional/shape-shifting molecules can be driven forward by chemoselective reduction to useful polyfunctionalized building blocks.

Original language	English (US)
Pages (from-to)	1951-1956
Number of pages	6
Journal	Chemical Science
Volume	13
Issue number	7
DOIs	https://doi.org/10.1039/d1sc06307c
State	Published - Feb 21 2022
Externally published	Yes

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© The Royal Society of Chemistry.

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10.1039/d1sc06307c

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abstract = "Herein reported is a strategy for constructing vicinal 4°/3° carbons via reductive Cope rearrangement. Substrates have been designed which exhibit Cope rearrangement kinetic barriers of ∼23 kcal mol-1 with isoenergetic favorability (ΔG ∼ 0). These fluxional/shape-shifting molecules can be driven forward by chemoselective reduction to useful polyfunctionalized building blocks.",

author = "Sobie, \{Kristin M.\} and Matthew Albritton and Yinuo Yang and Alves, \{Mariana M.\} and Adrian Roitberg and Grenning, \{Alexander J.\}",

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doi = "10.1039/d1sc06307c",

language = "English (US)",

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T1 - Construction of vicinal 4°/3°-carbons

T2 - Via reductive Cope rearrangement

AU - Sobie, Kristin M.

AU - Albritton, Matthew

AU - Yang, Yinuo

AU - Alves, Mariana M.

AU - Roitberg, Adrian

AU - Grenning, Alexander J.

PY - 2022/2/21

Y1 - 2022/2/21

N2 - Herein reported is a strategy for constructing vicinal 4°/3° carbons via reductive Cope rearrangement. Substrates have been designed which exhibit Cope rearrangement kinetic barriers of ∼23 kcal mol-1 with isoenergetic favorability (ΔG ∼ 0). These fluxional/shape-shifting molecules can be driven forward by chemoselective reduction to useful polyfunctionalized building blocks.

AB - Herein reported is a strategy for constructing vicinal 4°/3° carbons via reductive Cope rearrangement. Substrates have been designed which exhibit Cope rearrangement kinetic barriers of ∼23 kcal mol-1 with isoenergetic favorability (ΔG ∼ 0). These fluxional/shape-shifting molecules can be driven forward by chemoselective reduction to useful polyfunctionalized building blocks.

UR - https://www.scopus.com/pages/publications/85125091148

UR - https://www.scopus.com/pages/publications/85125091148#tab=citedBy

U2 - 10.1039/d1sc06307c

DO - 10.1039/d1sc06307c

M3 - Article

AN - SCOPUS:85125091148

SN - 2041-6520

VL - 13

SP - 1951

EP - 1956

JO - Chemical Science

JF - Chemical Science

IS - 7

ER -

Construction of vicinal 4°/3°-carbons: Via reductive Cope rearrangement

Abstract

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