Diastereoselective hydroxymethylation of cyclic N-tert- butanesulfinylketimines using methoxymethanol as formaldehyde source

Martins Priede; Mihail Kazak; Toms Kalnins; Kirill Shubin; Edgars Suna

doi:10.1021/jo500506u

Diastereoselective hydroxymethylation of cyclic N-tert- butanesulfinylketimines using methoxymethanol as formaldehyde source

Martins Priede
, Mihail Kazak
, Toms Kalnins
, Kirill Shubin
, Edgars Suna^*

^*Corresponding author for this work

Latvian Institute of Organic Synthesis

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

18 Citations (Scopus)

Abstract

Hydroxymethylation of cyclic tert-butanesulfinylketimine-derived lithium enamides with methoxymethanol proceeds with excellent diastereoselectivity (99:1 dr). Methoxymethanol is a stable and easy-to-handle source of anhydrous monomeric formaldehyde in the reaction with lithium enamides. Cyclic α-hydroxymethyl ketimines undergo highly diastereoselective reduction to syn- or anti-1,3-amino alcohols.

Original language	English
Pages (from-to)	3715-3724
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	79
Issue number	8
DOIs	https://doi.org/10.1021/jo500506u
Publication status	Published - 18 Apr 2014
Externally published	Yes

OECD Field of Science

1.4 Chemical Sciences

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10.1021/jo500506u

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title = "Diastereoselective hydroxymethylation of cyclic N-tert- butanesulfinylketimines using methoxymethanol as formaldehyde source",

abstract = "Hydroxymethylation of cyclic tert-butanesulfinylketimine-derived lithium enamides with methoxymethanol proceeds with excellent diastereoselectivity (99:1 dr). Methoxymethanol is a stable and easy-to-handle source of anhydrous monomeric formaldehyde in the reaction with lithium enamides. Cyclic α-hydroxymethyl ketimines undergo highly diastereoselective reduction to syn- or anti-1,3-amino alcohols.",

author = "Martins Priede and Mihail Kazak and Toms Kalnins and Kirill Shubin and Edgars Suna",

year = "2014",

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doi = "10.1021/jo500506u",

language = "English",

volume = "79",

pages = "3715--3724",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

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T1 - Diastereoselective hydroxymethylation of cyclic N-tert- butanesulfinylketimines using methoxymethanol as formaldehyde source

AU - Priede, Martins

AU - Kazak, Mihail

AU - Kalnins, Toms

AU - Shubin, Kirill

AU - Suna, Edgars

PY - 2014/4/18

Y1 - 2014/4/18

N2 - Hydroxymethylation of cyclic tert-butanesulfinylketimine-derived lithium enamides with methoxymethanol proceeds with excellent diastereoselectivity (99:1 dr). Methoxymethanol is a stable and easy-to-handle source of anhydrous monomeric formaldehyde in the reaction with lithium enamides. Cyclic α-hydroxymethyl ketimines undergo highly diastereoselective reduction to syn- or anti-1,3-amino alcohols.

AB - Hydroxymethylation of cyclic tert-butanesulfinylketimine-derived lithium enamides with methoxymethanol proceeds with excellent diastereoselectivity (99:1 dr). Methoxymethanol is a stable and easy-to-handle source of anhydrous monomeric formaldehyde in the reaction with lithium enamides. Cyclic α-hydroxymethyl ketimines undergo highly diastereoselective reduction to syn- or anti-1,3-amino alcohols.

UR - https://www.scopus.com/pages/publications/84898970488

U2 - 10.1021/jo500506u

DO - 10.1021/jo500506u

M3 - Article

C2 - 24666312

AN - SCOPUS:84898970488

SN - 0022-3263

VL - 79

SP - 3715

EP - 3724

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 8

ER -

Diastereoselective hydroxymethylation of cyclic N-tert- butanesulfinylketimines using methoxymethanol as formaldehyde source

Abstract

OECD Field of Science

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