Inter- and intramolecular [4 + 3] cycloadditions using epoxy enol silanes as functionalized oxyallyl cation precursors

Wing Ki Chung; Sze Kui Lam; Brian Lo; Lok Lok Liu; Wing Tak Wong; Pauline Chiu

doi:10.1021/ja807566t

Inter- and intramolecular [4 + 3] cycloadditions using epoxy enol silanes as functionalized oxyallyl cation precursors

Wing Ki Chung, Sze Kui Lam, Brian Lo, Lok Lok Liu, Wing Tak Wong, Pauline Chiu

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

70 Citations (Scopus)

Abstract

Using epoxy enol triethylsilanes as oxyallyl cation precursors, [4 + 3] cycloadditions with various dienes occur under catalysis by silyl triflates and acids in good yields. The intramolecular [4 + 3] cycloaddition proceeds under mild conditions and generate hydroxylated cycloadducts with high diastereoselectivity and yields. Enantiomerically pure epoxy enol silanes have been shown to give excellent yields of the optically pure cycloadduct bearing multiple stereocenters.

Original language	English
Pages (from-to)	4556-4557
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	131
Issue number	13
DOIs	https://doi.org/10.1021/ja807566t
Publication status	Published - 8 Apr 2009
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja807566t

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abstract = "Using epoxy enol triethylsilanes as oxyallyl cation precursors, [4 + 3] cycloadditions with various dienes occur under catalysis by silyl triflates and acids in good yields. The intramolecular [4 + 3] cycloaddition proceeds under mild conditions and generate hydroxylated cycloadducts with high diastereoselectivity and yields. Enantiomerically pure epoxy enol silanes have been shown to give excellent yields of the optically pure cycloadduct bearing multiple stereocenters.",

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AU - Liu, Lok Lok

AU - Wong, Wing Tak

AU - Chiu, Pauline

PY - 2009/4/8

Y1 - 2009/4/8

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AB - Using epoxy enol triethylsilanes as oxyallyl cation precursors, [4 + 3] cycloadditions with various dienes occur under catalysis by silyl triflates and acids in good yields. The intramolecular [4 + 3] cycloaddition proceeds under mild conditions and generate hydroxylated cycloadducts with high diastereoselectivity and yields. Enantiomerically pure epoxy enol silanes have been shown to give excellent yields of the optically pure cycloadduct bearing multiple stereocenters.

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ER -

Inter- and intramolecular [4 + 3] cycloadditions using epoxy enol silanes as functionalized oxyallyl cation precursors

Abstract

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