Free radical hydrostannylation of unactivated alkenes with chiral trialkylstannanes

Yvonne Kavanagh; Leigh Ford; Carl Herbert Schiesser

doi:10.1021/om200473c

Free radical hydrostannylation of unactivated alkenes with chiral trialkylstannanes

Yvonne Kavanagh, Leigh Ford, Carl Herbert Schiesser

Medicinal Chemistry

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

8 Citations (Scopus)

Abstract

Free radical hydrostannylation of olefins with differing steric and electronic demands have been carried out using the chiral, nonracemic stannanes (1R,2S,5R)-menthyldiphenyltin hydride (7), bis[(1R,2S,5R)-menthyl]phenyltin hydride (8), and tris[(1R,2S,5R)-menthyl]tin hydride (9). These reactions resulted in adducts 16-18 with yields that were found to depend on the nature of the substituents on both alkene and stannane and could be carried out at low temperature initiated by triethylborane and oxygen; MenPh₂SnH (7) reacted with tert-butyldimethyl(1-phenylvinyloxy)silane (1) at -78 °C to afford adduct 19 in near-quantitative yield. Somewhat surprisingly, addition of small quantities of diphenyl diselenide to these reactions failed to improve the outcome under any circumstances.

Original language	English
Pages (from-to)	4387-4392
Number of pages	6
Journal	Organometallics
Volume	30
Issue number	16
DOIs	https://doi.org/10.1021/om200473c
Publication status	Published - 22 Aug 2011

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abstract = "Free radical hydrostannylation of olefins with differing steric and electronic demands have been carried out using the chiral, nonracemic stannanes (1R,2S,5R)-menthyldiphenyltin hydride (7), bis[(1R,2S,5R)-menthyl]phenyltin hydride (8), and tris[(1R,2S,5R)-menthyl]tin hydride (9). These reactions resulted in adducts 16-18 with yields that were found to depend on the nature of the substituents on both alkene and stannane and could be carried out at low temperature initiated by triethylborane and oxygen; MenPh2SnH (7) reacted with tert-butyldimethyl(1-phenylvinyloxy)silane (1) at -78 °C to afford adduct 19 in near-quantitative yield. Somewhat surprisingly, addition of small quantities of diphenyl diselenide to these reactions failed to improve the outcome under any circumstances.",

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AU - Kavanagh, Yvonne

AU - Ford, Leigh

AU - Schiesser, Carl Herbert

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N2 - Free radical hydrostannylation of olefins with differing steric and electronic demands have been carried out using the chiral, nonracemic stannanes (1R,2S,5R)-menthyldiphenyltin hydride (7), bis[(1R,2S,5R)-menthyl]phenyltin hydride (8), and tris[(1R,2S,5R)-menthyl]tin hydride (9). These reactions resulted in adducts 16-18 with yields that were found to depend on the nature of the substituents on both alkene and stannane and could be carried out at low temperature initiated by triethylborane and oxygen; MenPh2SnH (7) reacted with tert-butyldimethyl(1-phenylvinyloxy)silane (1) at -78 °C to afford adduct 19 in near-quantitative yield. Somewhat surprisingly, addition of small quantities of diphenyl diselenide to these reactions failed to improve the outcome under any circumstances.

AB - Free radical hydrostannylation of olefins with differing steric and electronic demands have been carried out using the chiral, nonracemic stannanes (1R,2S,5R)-menthyldiphenyltin hydride (7), bis[(1R,2S,5R)-menthyl]phenyltin hydride (8), and tris[(1R,2S,5R)-menthyl]tin hydride (9). These reactions resulted in adducts 16-18 with yields that were found to depend on the nature of the substituents on both alkene and stannane and could be carried out at low temperature initiated by triethylborane and oxygen; MenPh2SnH (7) reacted with tert-butyldimethyl(1-phenylvinyloxy)silane (1) at -78 °C to afford adduct 19 in near-quantitative yield. Somewhat surprisingly, addition of small quantities of diphenyl diselenide to these reactions failed to improve the outcome under any circumstances.

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Free radical hydrostannylation of unactivated alkenes with chiral trialkylstannanes

Abstract

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