Diastereoselective and Enantiospecific Synthesis of 1,3-Diamines via 2-Azaallyl Anion Benzylic Ring-Opening of Aziridines.
Publication
, Journal Article
Li, K; Weber, AE; Tseng, L; Malcolmson, SJ
Published in: Organic letters
August 2017
The 1,3-diamine motif appears in numerous complex molecules, yet there are few methods for the stereoselective construction of this moiety. Herein, we demonstrate a stereocontrolled synthesis of 1,3-diamines, which bear up to three contiguous stereogenic centers, through benzylic ring-opening of aziridines with 2-azaallyl anion nucleophiles. Reactions proceed efficiently (yield up to 95%), diastereoselectively (dr up to >20:1), site selectively, and enantiospecifically to deliver products with differentiated amino groups.
Duke Scholars
Published In
Organic letters
DOI
EISSN
1523-7052
ISSN
1523-7060
Publication Date
August 2017
Volume
19
Issue
16
Start / End Page
4239 / 4242
Related Subject Headings
- Organic Chemistry
- 34 Chemical sciences
- 03 Chemical Sciences
Citation
APA
Chicago
ICMJE
MLA
NLM
Li, K., Weber, A. E., Tseng, L., & Malcolmson, S. J. (2017). Diastereoselective and Enantiospecific Synthesis of 1,3-Diamines via 2-Azaallyl Anion Benzylic Ring-Opening of Aziridines. Organic Letters, 19(16), 4239–4242. https://doi.org/10.1021/acs.orglett.7b01886
Li, Kangnan, Alexandria E. Weber, Luke Tseng, and Steven J. Malcolmson. “Diastereoselective and Enantiospecific Synthesis of 1,3-Diamines via 2-Azaallyl Anion Benzylic Ring-Opening of Aziridines.” Organic Letters 19, no. 16 (August 2017): 4239–42. https://doi.org/10.1021/acs.orglett.7b01886.
Li K, Weber AE, Tseng L, Malcolmson SJ. Diastereoselective and Enantiospecific Synthesis of 1,3-Diamines via 2-Azaallyl Anion Benzylic Ring-Opening of Aziridines. Organic letters. 2017 Aug;19(16):4239–42.
Li, Kangnan, et al. “Diastereoselective and Enantiospecific Synthesis of 1,3-Diamines via 2-Azaallyl Anion Benzylic Ring-Opening of Aziridines.” Organic Letters, vol. 19, no. 16, Aug. 2017, pp. 4239–42. Epmc, doi:10.1021/acs.orglett.7b01886.
Li K, Weber AE, Tseng L, Malcolmson SJ. Diastereoselective and Enantiospecific Synthesis of 1,3-Diamines via 2-Azaallyl Anion Benzylic Ring-Opening of Aziridines. Organic letters. 2017 Aug;19(16):4239–4242.
Published In
Organic letters
DOI
EISSN
1523-7052
ISSN
1523-7060
Publication Date
August 2017
Volume
19
Issue
16
Start / End Page
4239 / 4242
Related Subject Headings
- Organic Chemistry
- 34 Chemical sciences
- 03 Chemical Sciences