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Roush Crotylboration
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Abstract
This reaction is an enantioselective synthesis of a chiral alcohol by the condensation between a crotylboronate derived from diisopropyl‐(
R
,
R
)‐tartrate and an achiral aldehyde. This reaction is generally referred to as the Roush crotylboration. The synthesis of the (
Z
)‐ or (
E
)‐ from diisopropyl‐(
R
,
R
)‐tartrate has been discussed and the initial configuration of 2‐butene is preserved during the preparation. The study finds that these crotylboronates can yield only good to moderate enantioselectivity for the addition to most achiral aldehydes. Based on this reaction mechanism, a second generation of crotylboronates with a chiral auxiliary of (
R
,
R
)‐
N
,
N
′‐bis‐(2,2,2‐trifluoroethyl)‐
N
,
N
′‐ethylenetartramide has been developed. This reaction has wide application in asymmetric synthesis.
Title: Roush Crotylboration
Description:
Abstract
This reaction is an enantioselective synthesis of a chiral alcohol by the condensation between a crotylboronate derived from diisopropyl‐(
R
,
R
)‐tartrate and an achiral aldehyde.
This reaction is generally referred to as the Roush crotylboration.
The synthesis of the (
Z
)‐ or (
E
)‐ from diisopropyl‐(
R
,
R
)‐tartrate has been discussed and the initial configuration of 2‐butene is preserved during the preparation.
The study finds that these crotylboronates can yield only good to moderate enantioselectivity for the addition to most achiral aldehydes.
Based on this reaction mechanism, a second generation of crotylboronates with a chiral auxiliary of (
R
,
R
)‐
N
,
N
′‐bis‐(2,2,2‐trifluoroethyl)‐
N
,
N
′‐ethylenetartramide has been developed.
This reaction has wide application in asymmetric synthesis.
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