Practical asymmetric synthesis of β-hydroxy γ-amino acids via complimentary aldol reactions

Orthogonally protected chiral β-hydroxy-γ-amino acids can be accessed in >100 g quantities from readily available starting materials and reagents in three to four steps. These chiral synthons contain two adjacent stereocenters along with suitably protected functional groups ( O-TBS, N-Boc) for do...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron Vol. 67; no. 34; pp. 6131 - 6137
Main Authors: Pandya, Bhaumik A., Dandapani, Sivaraman, Duvall, Jeremy R., Rowley, Ann, Mulrooney, Carol A., Ryba, Troy, Dombrowski, Michael, Harton, Marie, Young, Damian W., Marcaurelle, Lisa A.
Format: Journal Article
Language:English
Published: Kidlington Elsevier Ltd 26-08-2011
Elsevier
Subjects:
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Orthogonally protected chiral β-hydroxy-γ-amino acids can be accessed in >100 g quantities from readily available starting materials and reagents in three to four 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 one to two steps demonstrates their synthetic utility. [Display omitted]
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
Current address: H3 Biomedicine Inc., 300 Technology Square, Cambridge, MA 02139
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.06.043