Unexpected diastereoselectivity in AD of an L-proline-derived 1,1- disubstituted alkene

John M. Gardiner; Sarah E. Bruce

doi:10.1016/S0040-4039(97)10695-5

Unexpected diastereoselectivity in AD of an L-proline-derived 1,1- disubstituted alkene

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Abstract

Asymmetric dihydroxylation of the L-proline-derived 1,1-disubstituted alkene 5 catalysed by either (DHQ)2PHAL or (DHQD)2PHAL unexpectedly leads to preference for the same diastereomer 7, both reactions proceeding with apparently matching double diastereoselectivity. In contrast, AD using the analogous (DHQ)2PYR or (DHQD)2PYR ligands leads to preferences for diols 7 or 8 respectively.

Original language	English
Pages (from-to)	1029-1032
Number of pages	3
Journal	Tetrahedron Letters
Volume	39
Issue number	9
DOIs	https://doi.org/10.1016/S0040-4039(97)10695-5
Publication status	Published - 26 Feb 1998

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title = "Unexpected diastereoselectivity in AD of an L-proline-derived 1,1- disubstituted alkene",

abstract = "Asymmetric dihydroxylation of the L-proline-derived 1,1-disubstituted alkene 5 catalysed by either (DHQ)2PHAL or (DHQD)2PHAL unexpectedly leads to preference for the same diastereomer 7, both reactions proceeding with apparently matching double diastereoselectivity. In contrast, AD using the analogous (DHQ)2PYR or (DHQD)2PYR ligands leads to preferences for diols 7 or 8 respectively.",

author = "Gardiner, {John M.} and Bruce, {Sarah E.}",

year = "1998",

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doi = "10.1016/S0040-4039(97)10695-5",

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journal = "Tetrahedron Letters",

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AU - Gardiner, John M.

AU - Bruce, Sarah E.

PY - 1998/2/26

Y1 - 1998/2/26

N2 - Asymmetric dihydroxylation of the L-proline-derived 1,1-disubstituted alkene 5 catalysed by either (DHQ)2PHAL or (DHQD)2PHAL unexpectedly leads to preference for the same diastereomer 7, both reactions proceeding with apparently matching double diastereoselectivity. In contrast, AD using the analogous (DHQ)2PYR or (DHQD)2PYR ligands leads to preferences for diols 7 or 8 respectively.

AB - Asymmetric dihydroxylation of the L-proline-derived 1,1-disubstituted alkene 5 catalysed by either (DHQ)2PHAL or (DHQD)2PHAL unexpectedly leads to preference for the same diastereomer 7, both reactions proceeding with apparently matching double diastereoselectivity. In contrast, AD using the analogous (DHQ)2PYR or (DHQD)2PYR ligands leads to preferences for diols 7 or 8 respectively.

U2 - 10.1016/S0040-4039(97)10695-5

DO - 10.1016/S0040-4039(97)10695-5

M3 - Article

SN - 1873-3581

VL - 39

SP - 1029

EP - 1032

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 9

ER -

Unexpected diastereoselectivity in AD of an L-proline-derived 1,1- disubstituted alkene

Abstract

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