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加纳尔醛作为一种多功能中间体，在合成手性纯天然产物中的应用。

Garner's aldehyde as a versatile intermediate in the synthesis of enantiopure natural products.

机构信息

Aalto-University, School of Chemical Technology, Department of Chemistry P.O. Box 16100 (Kemistintie 1), FI-00076 Aalto, Finland.

出版信息

Beilstein J Org Chem. 2013 Nov 26;9:2641-59. doi: 10.3762/bjoc.9.300.

DOI:10.3762/bjoc.9.300
PMID:24367429
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3869249/
Abstract

Since its introduction to the synthetic community in 1984, Garner's aldehyde has gained substantial attention as a chiral intermediate for the synthesis of numerous amino alcohol derivatives. This review presents some of the most successful carbon chain elongation reactions, namely carbonyl alkylations and olefinations. The literature is reviewed with particular attention on understanding how to avoid the deleterious epimerization of the existing stereocenter in Garner's aldehyde.

摘要

自 1984 年引入合成领域以来，Garner 醛作为合成众多氨基醇衍生物的手性中间体，受到了广泛关注。本文综述了一些最成功的碳链延长反应，即羰基烷基化和烯烃化反应。本文特别关注如何避免 Garner 醛中现有手性中心的有害差向异构化，对文献进行了综述。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/6c7e4abf2ba3/Beilstein_J_Org_Chem-09-2641-g019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/209fa6b09c04/Beilstein_J_Org_Chem-09-2641-g002.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/ab06d57f8ebc/Beilstein_J_Org_Chem-09-2641-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/d27e10ef4ec2/Beilstein_J_Org_Chem-09-2641-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/1bb6f8241201/Beilstein_J_Org_Chem-09-2641-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/6c18c06b5948/Beilstein_J_Org_Chem-09-2641-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/34f78320339c/Beilstein_J_Org_Chem-09-2641-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/285773438e1d/Beilstein_J_Org_Chem-09-2641-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/66745e1c428c/Beilstein_J_Org_Chem-09-2641-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/12a56480722a/Beilstein_J_Org_Chem-09-2641-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/7dc9aca3205e/Beilstein_J_Org_Chem-09-2641-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/d20adc55d4da/Beilstein_J_Org_Chem-09-2641-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/d179b4b0845e/Beilstein_J_Org_Chem-09-2641-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/9b8adbd9ffd8/Beilstein_J_Org_Chem-09-2641-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/0d7e506f1bea/Beilstein_J_Org_Chem-09-2641-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/a15887252893/Beilstein_J_Org_Chem-09-2641-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/5058020c5a6f/Beilstein_J_Org_Chem-09-2641-g018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/6c7e4abf2ba3/Beilstein_J_Org_Chem-09-2641-g019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/209fa6b09c04/Beilstein_J_Org_Chem-09-2641-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/01f24eb18451/Beilstein_J_Org_Chem-09-2641-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/ab06d57f8ebc/Beilstein_J_Org_Chem-09-2641-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/d27e10ef4ec2/Beilstein_J_Org_Chem-09-2641-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/1bb6f8241201/Beilstein_J_Org_Chem-09-2641-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/6c18c06b5948/Beilstein_J_Org_Chem-09-2641-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/34f78320339c/Beilstein_J_Org_Chem-09-2641-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/285773438e1d/Beilstein_J_Org_Chem-09-2641-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/66745e1c428c/Beilstein_J_Org_Chem-09-2641-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/12a56480722a/Beilstein_J_Org_Chem-09-2641-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/7dc9aca3205e/Beilstein_J_Org_Chem-09-2641-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/d20adc55d4da/Beilstein_J_Org_Chem-09-2641-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/d179b4b0845e/Beilstein_J_Org_Chem-09-2641-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/9b8adbd9ffd8/Beilstein_J_Org_Chem-09-2641-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/0d7e506f1bea/Beilstein_J_Org_Chem-09-2641-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/a15887252893/Beilstein_J_Org_Chem-09-2641-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/5058020c5a6f/Beilstein_J_Org_Chem-09-2641-g018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/04f5/3869249/6c7e4abf2ba3/Beilstein_J_Org_Chem-09-2641-g019.jpg

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