One-pot highly enantio- and diastereoselective synthesis of anti,anti vinylic 3-amino-1,2 diols via proline catalyzed sequential α-amination/ benzoyloxyallylation of aldehydes

Brij Bhushan Ahuja; Arumugam Sudalai

doi:10.1039/c5ra02830b

One-pot highly enantio- and diastereoselective synthesis of anti,anti vinylic 3-amino-1,2 diols via proline catalyzed sequential α-amination/ benzoyloxyallylation of aldehydes

Brij Bhushan Ahuja, Arumugam Sudalai^*

^*Corresponding author for this work

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

Abstract

The first direct asymmetric synthesis of anti,anti vinylic 3-amino-1,2-diols from aldehydes is described via a one-pot sequential l-proline catalyzed α-amination/benzoyloxyallylation protocol. The reaction proceeds with exceptionally high diastereoselectivity (>99%) as can be explained based on the Felkin-Ahn transition state model. Its effectiveness is proven unambiguously by demonstrating a short asymmetric synthesis of d-ribo-phytosphingosine tetraacetate (93% ee).

Original language	English
Pages (from-to)	21803-21805
Number of pages	3
Journal	RSC Advances
Volume	5
Issue number	28
DOIs	https://doi.org/10.1039/c5ra02830b
State	Published - 2015
Externally published	Yes

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title = "One-pot highly enantio- and diastereoselective synthesis of anti,anti vinylic 3-amino-1,2 diols via proline catalyzed sequential α-amination/ benzoyloxyallylation of aldehydes",

abstract = "The first direct asymmetric synthesis of anti,anti vinylic 3-amino-1,2-diols from aldehydes is described via a one-pot sequential l-proline catalyzed α-amination/benzoyloxyallylation protocol. The reaction proceeds with exceptionally high diastereoselectivity (>99%) as can be explained based on the Felkin-Ahn transition state model. Its effectiveness is proven unambiguously by demonstrating a short asymmetric synthesis of d-ribo-phytosphingosine tetraacetate (93% ee).",

author = "Ahuja, {Brij Bhushan} and Arumugam Sudalai",

note = "Publisher Copyright: {\textcopyright} 2015 The Royal Society of Chemistry.",

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doi = "10.1039/c5ra02830b",

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AU - Sudalai, Arumugam

PY - 2015

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N2 - The first direct asymmetric synthesis of anti,anti vinylic 3-amino-1,2-diols from aldehydes is described via a one-pot sequential l-proline catalyzed α-amination/benzoyloxyallylation protocol. The reaction proceeds with exceptionally high diastereoselectivity (>99%) as can be explained based on the Felkin-Ahn transition state model. Its effectiveness is proven unambiguously by demonstrating a short asymmetric synthesis of d-ribo-phytosphingosine tetraacetate (93% ee).

AB - The first direct asymmetric synthesis of anti,anti vinylic 3-amino-1,2-diols from aldehydes is described via a one-pot sequential l-proline catalyzed α-amination/benzoyloxyallylation protocol. The reaction proceeds with exceptionally high diastereoselectivity (>99%) as can be explained based on the Felkin-Ahn transition state model. Its effectiveness is proven unambiguously by demonstrating a short asymmetric synthesis of d-ribo-phytosphingosine tetraacetate (93% ee).

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ER -

One-pot highly enantio- and diastereoselective synthesis of anti,anti vinylic 3-amino-1,2 diols via proline catalyzed sequential α-amination/ benzoyloxyallylation of aldehydes

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