Grignard additions to α,β-unsaturated dioxolanones: Preparation of chiral allylic alcohols and protected α-hydroxy aldehydes

B. Heckmann; C. Mioskowski; Rama K. Bhatt; J R Falck

doi:10.1016/0040-4039(96)00058-5

Grignard additions to α,β-unsaturated dioxolanones: Preparation of chiral allylic alcohols and protected α-hydroxy aldehydes

B. Heckmann, C. Mioskowski, Rama K. Bhatt, J R Falck

Biochemistry

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

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Abstract

α,β-Unsaturated dioxolanones derived from mandelic acid smoothly add most Grignard reagents with good to excellent regio- and diastereoselectivities. The adducts are converted to chiral secondary alcohols by peroxidation at low temperature or to protected α-hydroxy aldehydes via ozonolysis.

Original language	English (US)
Pages (from-to)	1421-1424
Number of pages	4
Journal	Tetrahedron Letters
Volume	37
Issue number	9
DOIs	https://doi.org/10.1016/0040-4039(96)00058-5
State	Published - Feb 26 1996

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/0040-4039(96)00058-5

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title = "Grignard additions to α,β-unsaturated dioxolanones: Preparation of chiral allylic alcohols and protected α-hydroxy aldehydes",

abstract = "α,β-Unsaturated dioxolanones derived from mandelic acid smoothly add most Grignard reagents with good to excellent regio- and diastereoselectivities. The adducts are converted to chiral secondary alcohols by peroxidation at low temperature or to protected α-hydroxy aldehydes via ozonolysis.",

author = "B. Heckmann and C. Mioskowski and Bhatt, {Rama K.} and Falck, {J R}",

note = "Funding Information: Acknowledgments: Financial support was obtained from the USPHS NIH (GM31278) Welch Foundation I-0782.",

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T1 - Grignard additions to α,β-unsaturated dioxolanones

T2 - Preparation of chiral allylic alcohols and protected α-hydroxy aldehydes

AU - Heckmann, B.

AU - Mioskowski, C.

AU - Bhatt, Rama K.

AU - Falck, J R

N1 - Funding Information: Acknowledgments: Financial support was obtained from the USPHS NIH (GM31278) Welch Foundation I-0782.

PY - 1996/2/26

Y1 - 1996/2/26

N2 - α,β-Unsaturated dioxolanones derived from mandelic acid smoothly add most Grignard reagents with good to excellent regio- and diastereoselectivities. The adducts are converted to chiral secondary alcohols by peroxidation at low temperature or to protected α-hydroxy aldehydes via ozonolysis.

AB - α,β-Unsaturated dioxolanones derived from mandelic acid smoothly add most Grignard reagents with good to excellent regio- and diastereoselectivities. The adducts are converted to chiral secondary alcohols by peroxidation at low temperature or to protected α-hydroxy aldehydes via ozonolysis.

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U2 - 10.1016/0040-4039(96)00058-5

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JF - Tetrahedron Letters

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ER -

Grignard additions to α,β-unsaturated dioxolanones: Preparation of chiral allylic alcohols and protected α-hydroxy aldehydes

Abstract

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