Abstract
An efficient stereocontrolled synthesis of enantio-enriched N-Boc-N-allyl-α-amino alkylstannanes and N,N-diallylic α-amino alkylstannanes starting from enantio-enriched α-hydroxy alkylstannane has been developed. The aza-Wittig rearrangement of enantio-defined N,N-diallyl-α-amino alkyllithium, generated by tin-lithium exchange, is shown to proceed predominantly with inversion of configuration at the Li-bearing carbon terminus.
| Original language | English |
|---|---|
| Pages (from-to) | 1239-1242 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 44 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - Feb 3 2003 |
| Externally published | Yes |
All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Tomoyasu, T., Tomooka, K., & Nakai, T. (2003). Asymmetric synthesis of enantio-enriched acyclic α-amino alkylstannanes and rearrangement behavior of carbanions thereof. Tetrahedron Letters, 44(6), 1239-1242. https://doi.org/10.1016/S0040-4039(02)02811-3