| Practical asymmetric synthesis of β-hydroxy γ-amino acids via complimentary aldol reactions. | |
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MedLine Citation:
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PMID: 21822337 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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Orthogonally protected chiral β-hydroxy-γ-amino acids can be accessed in >100 g quantities from readily available starting materials and reagents in 3-4 steps. These chiral synthons contain two adjacent stereocenters along with suitably protected functional groups (O-TBS, N-Boc) for downstream reactivity. Implementation of two existing aldol technologies allows rapid access to all possible stereoisomers of 1. The guiding principles during reaction optimization were reaction scalability and operational efficiency. Conversion of the amino acids to a variety of chiral building blocks in 1-2 steps demonstrates their synthetic utility. |
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Authors:
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Bhaumik A Pandya; Sivaraman Dandapani; Jeremy R Duvall; Ann Rowley; Carol A Mulrooney; Troy Ryba; Michael Dombrowski; Marie Harton; Damian W Young; Lisa A Marcaurelle |
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Publication Detail:
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Type: JOURNAL ARTICLE |
Journal Detail:
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Title: Tetrahedron Volume: 67 ISSN: 0040-4020 ISO Abbreviation: - Publication Date: 2011 Aug |
Date Detail:
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Created Date: 2011-8-8 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2984170R Medline TA: Tetrahedron Country: - |
Other Details:
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Languages: ENG Pagination: 6131-6137 Citation Subset: - |
Affiliation:
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Chemical Biology Platform, The Broad Institute of MIT and Harvard, 7 Cambridge Center, Cambridge, MA 02142, USA. |
Export Citation:
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Descriptor/Qualifier:
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| Grant Support | |
ID/Acronym/Agency:
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P50 GM069721-11//NIGMS NIH HHS; RL1 HG004671-05//NHGRI NIH HHS |
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