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

TETRAHEDRON

卷:67

Article

Pandya, Bhaumik A.¹  Dandapani, Sivaraman¹  Duvall, Jeremy R.¹  Rowley, Ann¹  Mulrooney, Carol A.¹  Ryba, Troy¹  Dombrowski, Michael¹  Harton, Marie¹  Young, Damian W.¹  Marcaurelle, Lisa A.¹ 

[1] Broad Inst MIT & Harvard, Cambridge, MA 02142 USA

关键词: Aldol;    Asymmetric;    Stereochemistry;    gamma-Amino acid;    Diversity-oriented;   

DOI  :  10.1016/j.tet.2011.06.043

来源: Elsevier

【 摘 要 】

Orthogonally protected chiral beta-hydroxy-gamma-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 stereo-isomers 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. (C) 2011 Elsevier Ltd. All rights reserved.

【 授权许可】

Free