Highly selective α-acylvinyl anion additions to imines

Troy E. Reynolds; Michael S. Binkley; Karl A. Scheidt

doi:10.1021/ol802227t

Highly selective α-acylvinyl anion additions to imines

Troy E. Reynolds^*, Michael S. Binkley, Karl A. Scheidt

^*Corresponding author for this work

Chemistry

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

26 Scopus citations

Abstract

α-Hydroxypropargylsilanes undergo rearrangement to form reactive lithium allenolates. The resulting ∞-acylvinyl anion equivalents undergo highly selective additions to N-tert-butanesulfinyl imines generating/β- substituted aza-MBH-type products. High yields are achieved for a wide range of α-hydroxypropargylsilanes as well as for a diverse selection of imines. The reactions proceed with good to excellent diastereoselectivity and regioselectivity (8-20:1 major/Σ minor) favoring the Z-isomer of the alkene.

Original language	English (US)
Pages (from-to)	5227-5230
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	22
DOIs	https://doi.org/10.1021/ol802227t
State	Published - Dec 1 2008

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "α-Hydroxypropargylsilanes undergo rearrangement to form reactive lithium allenolates. The resulting ∞-acylvinyl anion equivalents undergo highly selective additions to N-tert-butanesulfinyl imines generating/β- substituted aza-MBH-type products. High yields are achieved for a wide range of α-hydroxypropargylsilanes as well as for a diverse selection of imines. The reactions proceed with good to excellent diastereoselectivity and regioselectivity (8-20:1 major/Σ minor) favoring the Z-isomer of the alkene.",

author = "Reynolds, {Troy E.} and Binkley, {Michael S.} and Scheidt, {Karl A.}",

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T1 - Highly selective α-acylvinyl anion additions to imines

AU - Reynolds, Troy E.

AU - Binkley, Michael S.

AU - Scheidt, Karl A.

PY - 2008/12/1

Y1 - 2008/12/1

N2 - α-Hydroxypropargylsilanes undergo rearrangement to form reactive lithium allenolates. The resulting ∞-acylvinyl anion equivalents undergo highly selective additions to N-tert-butanesulfinyl imines generating/β- substituted aza-MBH-type products. High yields are achieved for a wide range of α-hydroxypropargylsilanes as well as for a diverse selection of imines. The reactions proceed with good to excellent diastereoselectivity and regioselectivity (8-20:1 major/Σ minor) favoring the Z-isomer of the alkene.

AB - α-Hydroxypropargylsilanes undergo rearrangement to form reactive lithium allenolates. The resulting ∞-acylvinyl anion equivalents undergo highly selective additions to N-tert-butanesulfinyl imines generating/β- substituted aza-MBH-type products. High yields are achieved for a wide range of α-hydroxypropargylsilanes as well as for a diverse selection of imines. The reactions proceed with good to excellent diastereoselectivity and regioselectivity (8-20:1 major/Σ minor) favoring the Z-isomer of the alkene.

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