Asymmetric synthesis of enantio-enriched acyclic α-amino alkylstannanes and rearrangement behavior of carbanions thereof

Takahiro Tomoyasu; Katsuhiko Tomooka; Takeshi Nakai

doi:10.1016/S0040-4039(02)02811-3

Asymmetric synthesis of enantio-enriched acyclic α-amino alkylstannanes and rearrangement behavior of carbanions thereof

Takahiro Tomoyasu, Katsuhiko Tomooka, Takeshi Nakai

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

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	https://doi.org/10.1016/S0040-4039(02)02811-3
Publication status	Published - Feb 3 2003
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(02)02811-3

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title = "Asymmetric synthesis of enantio-enriched acyclic α-amino alkylstannanes and rearrangement behavior of carbanions thereof",

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.",

author = "Takahiro Tomoyasu and Katsuhiko Tomooka and Takeshi Nakai",

note = "Funding Information: This research was supported by a Grant-in-Aid for Scientific Research (B) from the Ministry of Education, Culture, Sports, Science and Technology, Japan. ",

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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

N1 - Funding Information: This research was supported by a Grant-in-Aid for Scientific Research (B) from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

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.

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DO - 10.1016/S0040-4039(02)02811-3

M3 - Article

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EP - 1242

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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ER -

Asymmetric synthesis of enantio-enriched acyclic α-amino alkylstannanes and rearrangement behavior of carbanions thereof

Abstract

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