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Practical asymmetric synthesis of ?-hydroxy ?-amino acids via complimentary aldol reactions.

ABSTRACT: Orthogonally protected chiral ?-hydroxy-?-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.

SUBMITTER: Pandya BA

PROVIDER: S-EPMC3150486 | biostudies-literature | 2011 Aug

REPOSITORIES: biostudies-literature

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

Pandya Bhaumik A BA Dandapani Sivaraman S Duvall Jeremy R JR Rowley Ann A Mulrooney Carol A CA Ryba Troy T Dombrowski Michael M Harton Marie M Young Damian W DW Marcaurelle Lisa A LA

Tetrahedron 20110801 34

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 opera ...[more]

PMID: 21822337

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