Highly Stereoselective Aldol Condensation Using an Enantioselective Chiral Enolate

Satoru Masamune; Sk Asrof Ali; David L. Snitman; David S. Garvey

doi:10.1002/anie.198005571

Highly Stereoselective Aldol Condensation Using an Enantioselective Chiral Enolate

Satoru Masamune, Sk Asrof Ali, David L. Snitman, David S. Garvey^*

^*Corresponding author for this work

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

284 Scopus citations

Abstract

The 3,4‐stereochemistry of aldol adducts can now be controlled for the first time with the new, chiral, readily accessible enolate reagent 2; i.e. the chiral aldehyde 1 can be transformed both into 3,4‐anti‐ and into the 3,4‐syn‐aldol adduct, 3 and 4, as major product. 2a forms 3a and 4a in the ratio of 15:1, while 2b leads to 3b and 4b in the ratio of 1:10. (Figure Presented.)

Original language	English
Pages (from-to)	557-558
Number of pages	2
Journal	Angewandte Chemie - International Edition
Volume	19
Issue number	7
DOIs	https://doi.org/10.1002/anie.198005571
State	Published - Jul 1980
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry

Access to Document

10.1002/anie.198005571

Cite this

@article{c03ccb2d790f467082262d75e6c075b7,

title = "Highly Stereoselective Aldol Condensation Using an Enantioselective Chiral Enolate",

abstract = "The 3,4‐stereochemistry of aldol adducts can now be controlled for the first time with the new, chiral, readily accessible enolate reagent 2; i.e. the chiral aldehyde 1 can be transformed both into 3,4‐anti‐ and into the 3,4‐syn‐aldol adduct, 3 and 4, as major product. 2a forms 3a and 4a in the ratio of 15:1, while 2b leads to 3b and 4b in the ratio of 1:10. (Figure Presented.)",

author = "Satoru Masamune and Ali, \{Sk Asrof\} and Snitman, \{David L.\} and Garvey, \{David S.\}",

year = "1980",

month = jul,

doi = "10.1002/anie.198005571",

language = "English",

volume = "19",

pages = "557--558",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

number = "7",

}

TY - JOUR

T1 - Highly Stereoselective Aldol Condensation Using an Enantioselective Chiral Enolate

AU - Masamune, Satoru

AU - Ali, Sk Asrof

AU - Snitman, David L.

AU - Garvey, David S.

PY - 1980/7

Y1 - 1980/7

N2 - The 3,4‐stereochemistry of aldol adducts can now be controlled for the first time with the new, chiral, readily accessible enolate reagent 2; i.e. the chiral aldehyde 1 can be transformed both into 3,4‐anti‐ and into the 3,4‐syn‐aldol adduct, 3 and 4, as major product. 2a forms 3a and 4a in the ratio of 15:1, while 2b leads to 3b and 4b in the ratio of 1:10. (Figure Presented.)

AB - The 3,4‐stereochemistry of aldol adducts can now be controlled for the first time with the new, chiral, readily accessible enolate reagent 2; i.e. the chiral aldehyde 1 can be transformed both into 3,4‐anti‐ and into the 3,4‐syn‐aldol adduct, 3 and 4, as major product. 2a forms 3a and 4a in the ratio of 15:1, while 2b leads to 3b and 4b in the ratio of 1:10. (Figure Presented.)

UR - https://www.scopus.com/pages/publications/84985553225

U2 - 10.1002/anie.198005571

DO - 10.1002/anie.198005571

M3 - Article

AN - SCOPUS:84985553225

SN - 1433-7851

VL - 19

SP - 557

EP - 558

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 7

ER -

Highly Stereoselective Aldol Condensation Using an Enantioselective Chiral Enolate

Abstract

ASJC Scopus subject areas

Access to Document

Fingerprint

Cite this