Epoxy and aziridinyl enolsilanes in diastereoselective inter- and intramolecular Friedel-Crafts alkylations

Jesse Ling; Sze Kui Lam; Brian Lo; Sarah Lam; Wing Tak Wong; Jian Sun; Guanhua Chen; Pauline Chiu

doi:10.1039/c5qo00333d

Epoxy and aziridinyl enolsilanes in diastereoselective inter- and intramolecular Friedel-Crafts alkylations

Jesse Ling
, Sze Kui Lam
, Brian Lo
, Sarah Lam
, Wing Tak Wong
, Jian Sun
, Guanhua Chen
, Pauline Chiu

The Hong Kong Polytechnic University

Research output: Journal article publication › Journal article › Academic research › peer-review

19 Citations (Scopus)

Abstract

The Friedel-Crafts alkylations of epoxy enolsilanes with arenes occur under silyl triflate catalysis at low temperatures. Intermolecular alkylations with optically-enriched epoxides occur with conservation of ee. Intramolecular reactions give rise to cyclized products with high diastereoselectivity in good yields. Aziridinyl enolsilanes also undergo selective inter- and intramolecular Friedel-Crafts reactions in a similar manner.

Original language	English
Pages (from-to)	457-461
Number of pages	5
Journal	Organic Chemistry Frontiers
Volume	3
Issue number	4
DOIs	https://doi.org/10.1039/c5qo00333d
Publication status	Published - Apr 2016

ASJC Scopus subject areas

Organic Chemistry

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10.1039/c5qo00333d

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title = "Epoxy and aziridinyl enolsilanes in diastereoselective inter- and intramolecular Friedel-Crafts alkylations",

abstract = "The Friedel-Crafts alkylations of epoxy enolsilanes with arenes occur under silyl triflate catalysis at low temperatures. Intermolecular alkylations with optically-enriched epoxides occur with conservation of ee. Intramolecular reactions give rise to cyclized products with high diastereoselectivity in good yields. Aziridinyl enolsilanes also undergo selective inter- and intramolecular Friedel-Crafts reactions in a similar manner.",

author = "Jesse Ling and Lam, \{Sze Kui\} and Brian Lo and Sarah Lam and Wong, \{Wing Tak\} and Jian Sun and Guanhua Chen and Pauline Chiu",

note = "Funding Information: We thank the University of Hong Kong, The State Key Laboratory of Synthetic Chemistry, and the Hong Kong Research Grants Council General Research Fund (HKU 7016/12P) for financial support. We also thank Dr L. Szeto for collecting the X-ray diffraction data. J. L. thanks the University of Hong Kong for a conference grant. Publisher Copyright: {\textcopyright} 2016 the Partner Organisations.",

year = "2016",

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doi = "10.1039/c5qo00333d",

language = "English",

volume = "3",

pages = "457--461",

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T1 - Epoxy and aziridinyl enolsilanes in diastereoselective inter- and intramolecular Friedel-Crafts alkylations

AU - Ling, Jesse

AU - Lam, Sze Kui

AU - Lo, Brian

AU - Lam, Sarah

AU - Wong, Wing Tak

AU - Sun, Jian

AU - Chen, Guanhua

AU - Chiu, Pauline

N1 - Funding Information: We thank the University of Hong Kong, The State Key Laboratory of Synthetic Chemistry, and the Hong Kong Research Grants Council General Research Fund (HKU 7016/12P) for financial support. We also thank Dr L. Szeto for collecting the X-ray diffraction data. J. L. thanks the University of Hong Kong for a conference grant. Publisher Copyright: © 2016 the Partner Organisations.

PY - 2016/4

Y1 - 2016/4

N2 - The Friedel-Crafts alkylations of epoxy enolsilanes with arenes occur under silyl triflate catalysis at low temperatures. Intermolecular alkylations with optically-enriched epoxides occur with conservation of ee. Intramolecular reactions give rise to cyclized products with high diastereoselectivity in good yields. Aziridinyl enolsilanes also undergo selective inter- and intramolecular Friedel-Crafts reactions in a similar manner.

AB - The Friedel-Crafts alkylations of epoxy enolsilanes with arenes occur under silyl triflate catalysis at low temperatures. Intermolecular alkylations with optically-enriched epoxides occur with conservation of ee. Intramolecular reactions give rise to cyclized products with high diastereoselectivity in good yields. Aziridinyl enolsilanes also undergo selective inter- and intramolecular Friedel-Crafts reactions in a similar manner.

UR - https://www.scopus.com/pages/publications/84962439908

U2 - 10.1039/c5qo00333d

DO - 10.1039/c5qo00333d

M3 - Journal article

AN - SCOPUS:84962439908

SN - 2052-4110

VL - 3

SP - 457

EP - 461

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 4

ER -

Epoxy and aziridinyl enolsilanes in diastereoselective inter- and intramolecular Friedel-Crafts alkylations

Abstract

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