Dispiroketals in synthesis (part 10): Further reactions of dispoke protected lactate and glycolate enolates

Geert Jan Boons; Robert Downham; Kun Soo Kim; Steven V. Ley; Martin Woods

doi:10.1016/S0040-4020(01)85241-8

Dispiroketals in synthesis (part 10): Further reactions of dispoke protected lactate and glycolate enolates

Geert Jan Boons^*
, Robert Downham
, Kun Soo Kim
, Steven V. Ley
, Martin Woods

^*Corresponding author for this work

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

Abstract

α-Hydroxy acids have been reacted with bis-dihydropyrans to give dispiroketal adducts (1,8,13,16-tetraoxadispiro[5.0.5.4]-hexadecan-14-ones). The enolates derived from these compounds undergo reaction with electrophiles with generally high levels of diastereoselectivity. Subsequent deprotection of these compounds gives α-hydroxy esters of high enantiomeric excess.

Original language	English
Pages (from-to)	7157-7176
Number of pages	20
Journal	Tetrahedron
Volume	50
Issue number	24
DOIs	https://doi.org/10.1016/S0040-4020(01)85241-8
Publication status	Published - 1 Jan 1994
Externally published	Yes

Funding

Acknowledgements We thank the SERC (MW, RD). KOSEF (KSK) and the Ron~soy Menlorial Fund (G-JB) for financial support. We also gratefully acknowledge the B.P. endowment (to SVL) ut Cambridge.

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abstract = "α-Hydroxy acids have been reacted with bis-dihydropyrans to give dispiroketal adducts (1,8,13,16-tetraoxadispiro[5.0.5.4]-hexadecan-14-ones). The enolates derived from these compounds undergo reaction with electrophiles with generally high levels of diastereoselectivity. Subsequent deprotection of these compounds gives α-hydroxy esters of high enantiomeric excess.",

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AU - Kim, Kun Soo

AU - Ley, Steven V.

AU - Woods, Martin

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N2 - α-Hydroxy acids have been reacted with bis-dihydropyrans to give dispiroketal adducts (1,8,13,16-tetraoxadispiro[5.0.5.4]-hexadecan-14-ones). The enolates derived from these compounds undergo reaction with electrophiles with generally high levels of diastereoselectivity. Subsequent deprotection of these compounds gives α-hydroxy esters of high enantiomeric excess.

AB - α-Hydroxy acids have been reacted with bis-dihydropyrans to give dispiroketal adducts (1,8,13,16-tetraoxadispiro[5.0.5.4]-hexadecan-14-ones). The enolates derived from these compounds undergo reaction with electrophiles with generally high levels of diastereoselectivity. Subsequent deprotection of these compounds gives α-hydroxy esters of high enantiomeric excess.

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U2 - 10.1016/S0040-4020(01)85241-8

DO - 10.1016/S0040-4020(01)85241-8

M3 - Article

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JO - Tetrahedron

JF - Tetrahedron

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ER -

Dispiroketals in synthesis (part 10): Further reactions of dispoke protected lactate and glycolate enolates

Abstract

Funding

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