A novel domino reaction for the preparation of substituted non-racemic β-proline derivatives. Issue 40 (6th October 2016)

• Record Type: Journal Article
• Authors: Gilbert, Eric J.; Brunskill, Andrew; Cai, Jiaqiang; Cai, Yaxian; Chu, Xin-Jie; Dai, Xing; Hao, Jinsong; Kuethe, Jeffrey T.; Lai, Zhong; Liu, Hong; Mu, Cuizhi; Qi, Yan; Scott, Jack D.; Taoka, Brandon; Truong, Quang; Walsh, Shawn P.; Wu, Wen-Lian; Cumming, Jared N.
• Is Part Of: Tetrahedron. Volume 72:Issue 40(2016)
• Page Start: 6011
• Page End: 6020
• Publication Date: 2016-10-06
• Subjects: β-Proline -- Oxetane -- Domino reaction -- tert-Butanesulfinyl ketimine; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.08.017
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A novel domino reaction for the preparation of non-racemic β-proline derivatives is reported. The addition of a methyl 2-(oxetan-3-yl)acetate titanium enolate to chiral tert -butanesulfinyl ketimines followed by an intramolecular oxetane ring-opening provides the highly-substituted pyrrolidine ring systems with three contiguous stereogenic centers. Graphical abstract: