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 |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry
Cite this
Asymmetric synthesis of enantio-enriched acyclic α-amino alkylstannanes and rearrangement behavior of carbanions thereof. / Tomoyasu, Takahiro; Tomooka, Katsuhiko; Nakai, Takeshi.
In: Tetrahedron Letters, Vol. 44, No. 6, 03.02.2003, p. 1239-1242.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Asymmetric synthesis of enantio-enriched acyclic α-amino alkylstannanes and rearrangement behavior of carbanions thereof
AU - Tomoyasu, Takahiro
AU - Tomooka, Katsuhiko
AU - Nakai, Takeshi
PY - 2003/2/3
Y1 - 2003/2/3
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0037415462&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0037415462&partnerID=8YFLogxK
U2 - 10.1016/S0040-4039(02)02811-3
DO - 10.1016/S0040-4039(02)02811-3
M3 - Article
AN - SCOPUS:0037415462
VL - 44
SP - 1239
EP - 1242
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 6
ER -