"Super silyl" group for diastereoselective sequential reactions: access to complex chiral architecture in one pot | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

4077525

Reference Type

Journal Article

Title

"Super silyl" group for diastereoselective sequential reactions: access to complex chiral architecture in one pot

Author(s)

Boxer, MB; Yamamoto, H

Year

2007

Is Peer Reviewed?

Yes

Journal

Journal of the American Chemical Society
ISSN: 0002-7863
EISSN: 1520-5126

Volume

129

Issue

Page Numbers

2762-2763

Language

English

PMID

17309266

DOI

10.1021/ja0693542

Web of Science Id

WOS:000244731500018

URL

https://pubs.acs.org/doi/10.1021/ja0693542
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Abstract

We have shown that the tris(trimethylsilyl)silyl (TTMSS) silyl enol ether of acetaldehyde undergoes aldehyde cross-aldol reactions with high selectivity and the extremely low catalyst loading (0.05 mol % of HNTf2) allows for one-pot sequential reactions where acidic or basic nucleophiles can be subsequently added. Various ketone-derived silyl enol ethers, Grignard reagents, and dienes succeeded, generating relatively complex molecular architectures in a single step. This represents the first case where, in a single pot, highly acidic conditions followed by very basic conditions were tolerated to give products with high diastereoselectivities and good yields. Copyright © 2007 American Chemical Society.