Abstract
Copper-catalyzed γ-selective coupling between propargylic phosphates and alkylboron compounds (alkyl-9-BBN, prepared by hydroboration of alkenes with 9-BBN-H) affords multisubstituted allenes with various functional groups. The reaction of enantioenriched propargylic phosphates to give axially chiral allenes proceeds with excellent point-to-axial chirality transfer with 1,3-anti stereochemistry.
| Original language | English |
|---|---|
| Pages (from-to) | 6312-6315 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 13 |
| Issue number | 23 |
| DOIs | |
| Publication status | Published - Dec 2 2011 |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
General approach to allenes through copper-catalyzed γ-selective and stereospecific coupling between propargylic phosphates and alkylboranes. / Ohmiya, Hirohisa; Yokobori, Umi; Makida, Yusuke; Sawamura, Masaya.
In: Organic Letters, Vol. 13, No. 23, 02.12.2011, p. 6312-6315.Research output: Contribution to journal › Article
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TY - JOUR
T1 - General approach to allenes through copper-catalyzed γ-selective and stereospecific coupling between propargylic phosphates and alkylboranes
AU - Ohmiya, Hirohisa
AU - Yokobori, Umi
AU - Makida, Yusuke
AU - Sawamura, Masaya
PY - 2011/12/2
Y1 - 2011/12/2
N2 - Copper-catalyzed γ-selective coupling between propargylic phosphates and alkylboron compounds (alkyl-9-BBN, prepared by hydroboration of alkenes with 9-BBN-H) affords multisubstituted allenes with various functional groups. The reaction of enantioenriched propargylic phosphates to give axially chiral allenes proceeds with excellent point-to-axial chirality transfer with 1,3-anti stereochemistry.
AB - Copper-catalyzed γ-selective coupling between propargylic phosphates and alkylboron compounds (alkyl-9-BBN, prepared by hydroboration of alkenes with 9-BBN-H) affords multisubstituted allenes with various functional groups. The reaction of enantioenriched propargylic phosphates to give axially chiral allenes proceeds with excellent point-to-axial chirality transfer with 1,3-anti stereochemistry.
UR - http://www.scopus.com/inward/record.url?scp=82355160810&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=82355160810&partnerID=8YFLogxK
U2 - 10.1021/ol202866h
DO - 10.1021/ol202866h
M3 - Article
C2 - 22054013
AN - SCOPUS:82355160810
VL - 13
SP - 6312
EP - 6315
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 23
ER -