Enantiospecific Brook Rearrangement of Tertiary Benzylic α-Hydroxysilanes

Juan F. Collados; Pablo Ortiz; Juana M. Pérez; Yiyin Xia; Mark A.J. Koenis; Wybren J. Buma; Valentin P. Nicu; Syuzanna R. Harutyunyan

doi:10.1002/ejoc.201701469

Enantiospecific Brook Rearrangement of Tertiary Benzylic α-Hydroxysilanes

Juan F. Collados
, Pablo Ortiz
, Juana M. Pérez
, Yiyin Xia
, Mark A.J. Koenis
, Wybren J. Buma
, Valentin P. Nicu
, Syuzanna R. Harutyunyan^*

^*Corresponding author for this work

Bioeconomy and CO2

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

12 Citations (Scopus)

Abstract

The Brook rearrangement of simple, chiral tertiary benzylic α-hydroxysilanes is presented. The rearrangement followed by proton trapping is enantiospecific and proceeds with inversion of the configuration at the carbon center. Importantly, the [1,2]-Brook rearrangement can be followed by trapping of methyl or allyl electrophiles even in the protic environment, although with minimal retention of chirality.

Original language	English
Pages (from-to)	3900-3903
Number of pages	4
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	29
DOIs	https://doi.org/10.1002/ejoc.201701469
Publication status	Published - 7 Aug 2018

Keywords

Chirality
Enantiospecific
Hydroxysilanes
Rearrangement
Synthetic methods

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10.1002/ejoc.201701469

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title = "Enantiospecific Brook Rearrangement of Tertiary Benzylic α-Hydroxysilanes",

abstract = "The Brook rearrangement of simple, chiral tertiary benzylic α-hydroxysilanes is presented. The rearrangement followed by proton trapping is enantiospecific and proceeds with inversion of the configuration at the carbon center. Importantly, the [1,2]-Brook rearrangement can be followed by trapping of methyl or allyl electrophiles even in the protic environment, although with minimal retention of chirality.",

keywords = "Chirality, Enantiospecific, Hydroxysilanes, Rearrangement, Synthetic methods",

author = "Collados, \{Juan F.\} and Pablo Ortiz and P{\'e}rez, \{Juana M.\} and Yiyin Xia and Koenis, \{Mark A.J.\} and Buma, \{Wybren J.\} and Nicu, \{Valentin P.\} and Harutyunyan, \{Syuzanna R.\}",

note = "Publisher Copyright: {\textcopyright} 2018 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2018",

month = aug,

day = "7",

doi = "10.1002/ejoc.201701469",

language = "English",

volume = "2018",

pages = "3900--3903",

journal = "European Journal of Organic Chemistry",

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publisher = "Wiley-VCH Verlag",

number = "29",

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TY - JOUR

T1 - Enantiospecific Brook Rearrangement of Tertiary Benzylic α-Hydroxysilanes

AU - Collados, Juan F.

AU - Ortiz, Pablo

AU - Pérez, Juana M.

AU - Xia, Yiyin

AU - Koenis, Mark A.J.

AU - Buma, Wybren J.

AU - Nicu, Valentin P.

AU - Harutyunyan, Syuzanna R.

PY - 2018/8/7

Y1 - 2018/8/7

N2 - The Brook rearrangement of simple, chiral tertiary benzylic α-hydroxysilanes is presented. The rearrangement followed by proton trapping is enantiospecific and proceeds with inversion of the configuration at the carbon center. Importantly, the [1,2]-Brook rearrangement can be followed by trapping of methyl or allyl electrophiles even in the protic environment, although with minimal retention of chirality.

AB - The Brook rearrangement of simple, chiral tertiary benzylic α-hydroxysilanes is presented. The rearrangement followed by proton trapping is enantiospecific and proceeds with inversion of the configuration at the carbon center. Importantly, the [1,2]-Brook rearrangement can be followed by trapping of methyl or allyl electrophiles even in the protic environment, although with minimal retention of chirality.

KW - Chirality

KW - Enantiospecific

KW - Hydroxysilanes

KW - Rearrangement

KW - Synthetic methods

UR - https://www.scopus.com/pages/publications/85051137614

U2 - 10.1002/ejoc.201701469

DO - 10.1002/ejoc.201701469

M3 - Article

AN - SCOPUS:85051137614

SN - 1434-193X

VL - 2018

SP - 3900

EP - 3903

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 29

ER -

Enantiospecific Brook Rearrangement of Tertiary Benzylic α-Hydroxysilanes

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Keywords

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